Downside: It cuts into your bottom line increasing expenses, having to endure ridiculous rules that may not make sense to you or your tenants, restrictions on the number of units the HOA allow to be non-owner occupied (The HOA can decide to limit, reduce or expand the number of non-owner occupied units at any time).

Since you're in a college town, either one of these will take 3.5% down and allow you to purchase a building with up to 4 units.

That would give clarity to the situation at least as it concerns code violations, unapproved/permitted improvements and what will need to be done.I purchased a property in Pennsylvania with code violations and received a temporary U&O that allowed repairs, but not residential occupation. 

Always do a math analysis and try to look at the prospective properties before you make an offer or at least have a clause in the sales contract that allows you the time (usually about 15 days) to make a detailed inspection and possibly back out of the deal without a penalty that will hurt you too much.I went to college too (and it is not mandatory) and I got a business degree that emphasized real estate.  

I can't include my personal email address as it isn't allowed on bp (my email was flagged until I removed it).Have you ran into any problems with them during any wholesale transactions?  

The seller managed to purchase at a time where prices were still depressed and purchased through a short sale allowing a steep discount.

In doing so, I had to breakdown entire rehab into small jobs rather than allowing GC to bid entire job.

So, why not just borrow as much of a percentage as they will allow from the outset?...

Since I don't know the area in Orlando very well, I have a job that allows me to call anywhere home and the Orlando area is a place that I'd like to invest in due to its proximity to parks and a potential job offer for my significant other.

However, as @Andres Verney suggested, if you get a percentage off of other people's rentals, and roll that into your own, that could help you on your way and allow you to minimize the expenses on your own rentals.