My goal is to live-in one side, then after the two-three year period for FHA, move out and continue to generate cash flow.

The market seems likely to have continued long-term appreciation.

If in case you ever go through an eviction , section 8 will continue to pay during the period of an eviction up until tenant is out of your unit. 

I’ve been given advice to ‘keep buying’...My fist property will be working well with a cap of 7.7.ITs an Attractive idea, To pay it off, and Then leverage it.But I hear, I should continue Buying.Any Arguments, Either way?

I understand I will need liquid cash for repairs and such, but the bigger question is should I go where the properties are cheaper so my "risk" is less, or should I continue to wait until I have a much large amount of cash saved?

Near the schools in Tampa, they would be considered student housing, and that's a ton of wear and tear and turnover.I love, and will continue looking at small multi-families that are all 2/1. 

If you plan on continuing to invest and have a long-term perspective, then creating an Opportunity Fund and investing in an Opportunity Zone property might be a better solution.What is it that you want or need?

I've gotten quotes in the range of $3500 but continue to call local providers until I can find a company with a more reasonable rate. 

The more properties you flip will continually increase your chances of running into a property with a title problem.

It's really disappointing to see the City of Chicago continually supports the idea of the landlord and investor being the enemy for many pockets of the City.