I would be more than happy to discuss real estate market analysis and hear about your successes in other markets, as well as your experience with long-range investing.

But I also generally am investing in pure cash flow markets (The Midwest...except for some recent investments in Phoenix).If you stay around that 2-3% range, what's the worst that can happen?

I don’t like the numbers unless you can get close to rent in the 1700 range to cover closing cost and some rehab.  

There cost for these services range- and the lowest (which is what people are really interested in right) I have found is $500 for the qualifying process, which you would tack on to the closing costs.

And selling in that 700-900 range properties tend to sit a bit longer because there are less buyers in that price range.I have also considered building a spec home at a considerably lower price, and I am also toying with the idea of putting a manufactured home on it for around 100k and getting a quick return. 

Rents in my neighborhood go for 1600-1900My target range for the bigger house would be a max of 330k and I think could rent the bottom out for 800-1000 per month.Scenario 1: I rent out my old house, I factored in taxes,  insurance, 5% for vacancies and 5% for repairs and I'm estimating $150/month cash flow.My payments on the new place would be about $1750 - 900 from the tenant = $850/ month. 

If I find that I need a more comprehensive solution, I'll look into Buildium.  

It's possible to rent our home in the $3000 - 3200 range.

I’m seeking advice that can help me form a contract that is in basic comprehensive layman terms.

Tampa and the outskirts are good areas to start developing expertise in, there are growth areas all the way down to Fort Myers for your area.I would get clear about your property type/range - if you are focusing on one area only then make sure your area is forecast for some decent growth over the next 10 years if you are aiming to hold it and rent it.