...I am thinking of a long term hold and using rent to generate cash flow to build the equity and *maybe* extra left over. The goal is cash generation and MINIMAL repair work. My time is much more valuable growing a business and generating more income than doing a floor job that would looking like something helen keller would do!!
Then why not do what makes your time more valuable, and grow another business generating income instead of doing repair and maintenance work on Real Estate lol? If you hate repair and maintenance work, you will hate Real Estate. Even if you don't do it yourself and you pay to have someone else do it, that's still money that has to be invested in order to keep the property attractive to both current and prospective tenants.
You want to become a Real Estate Development Company, that's fine, how much capital do you have and where would it come from? How much experience do you have in Commercial Real Estate or Residential Real Estate as an Agent, Mortgage Broker, etc.? Who are your legal and financial advisers/professionals? Who does your market research, who is your market research team?
Perhaps the optimal path for this is to incorporate ( if others want to also do this) in an LLC. I have not done the DD and do not understand the tax implications or anything, but it seems that an LLC makes sense insomuch that we can either pay out vis dividend, or reinvest into the company and decrease our tax footprint.
An LLC is good to put a property into because, the LLC is the least expensive form of business incorporation, allowing you the benefits of a C-Corporation in terms of protection but the low costs of running the LLC similar to that of a Sole Prop. However, the LLC has to be structured in a certain way for the benefits to come to pass efficiently, if you haven't, you need to be speaking with a CPA that specializes in in Business Formation along with an Attorney that specializes in Business Law so that each LLC that the property sits in is setup properly. Also putting each property in its own LLC sheds other properties from the liabilities of THAT property and so on. If you will have multiple properties, one LLC formation to use is a Series LLC depending on your State.
Here is maybe where some of the pros could shed some light:
1- best way to generate cash flow in good areas. Not looking to buy in the slums and rent to degenerates.
Nobody will have an answer for this that makes any sense, has any level of efficiency, or has any amount of credibility. That's like asking a restaurant owner for his recipe, he will never tell you that. His recipe is a result of years of trial and error, taking this advice and that advice and piecing them together, market research, market timing, experience, education, etc.
Only YOU can answer this question, it's what makes you a Business Owner and everyone else NOT one, it's the fact that you have a secret recipe (in the form of a unique business plan) that no one else has that consistently produces revenues and returns. And when you develop your secret recipe/secret sauce, make sure you don't give it out.
3- Some reasonable models to incorporate realistic "Cost of business" so I can accurately gauge a wide range of potential investments and determine the "best" ( okay ideal) ones, and separate them from the sub optimal ones.
Again, nobody is going to do this for you in a form that has any amount of credibility, you must do your own analysis and scope of this inconjunction with working with your CPA.
My advice to you is to start doing your DD and DO NOT start investing in Real Estate Development in any form (unless it's a house you will live in). As I recommend to people, why not work for a Real Estate Developer? Learn the insides and out of the industry, learn what the legal implications are, tax procedures are, how to find a property worth investing in BASED on the focus of the Real Estate Developer (be a bird dog), etc.?
Or, become a Real Estate Agent, or a Commercial Mortgage Broker, or a Residential Mortgage Broker, do something in Real Estate for at least 5 - 10 years to learn the damn industry. These damn infomercials on TV and all over the internet has everybody talking about "Real Estate is the ideal thing to do," well how in the hell do you know that? Who goes out and OPENS a restaurant before having WORKED for one?
Succeeding in Real Estate Development is significantly more complicated than it's promoted to be, it's perhaps one of the MOST complicated forms of businesses to succeed in. No one without any strong Real Estate background should EVER attempt to do it.