@Tony C. remember the advice: "Don't bet long term with short term money." 

FYI - City marine, and I assume others, charge a primium to owners who do short term rentals.  

Your better bet is with the income from the business and adding back any depreciation expense you are claiming. 

@Aaron Van Curen Is there a reason you're charging yourself to preform services on your own properties? 

Most investors start with "house hacking", getting a 2-4plex and then renting out the other units and owner-occupy one of them.yes, buying and renting out property is a wise idea as long as you rent to good tenants and charge them sufficient rents to justify the cost of owning the property.

i'm wondering if i invested to fix up the place and make it very nice, and wanted to get better tenants, what would be the most i could charge rent in that area?  

Liens may have been wiped out in the foreclosure depending on the laws of your state, or there may be a limit to how much the HOA can charge after a foreclosure. 

I bet if you buy multiple, either company would give you a small break on them.

Have the buyer put 20% down and charge them a higher interest than you pay a monthly in PITI. 

Also if and when you decide to move out the unit would be able to charge market rent.