I'm contemplating building my own house with the subs we use.

I am investor looking to buy the first rental property that I do not live in, and I have been contemplating getting a real estate license.

Jennifer Castle as I'm sure you've heard, short term rentals like AirBnB are under assault by the city for non-payment of hotel tax.

I've done it with tax deed properties during the redemption period, but never contemplated just finding a vacant house and taking over.  

It sounds at the surface like what you should be considering is another 1031 exchange to move into those new properties you are contemplating.

I am also contemplating on taking some carpentry classes at a local trade school so I can legitimately do some of the renovation work myself, and eventually become my own licensed general contractor. 

Don't even apply for other financing until you have past your loan closing, it's not just a ding on credit, not disclosing anticipated debt can give you a real problem, so give yourself enough time to have discovered your next deal , not in contemplation of creating more debt prior to closing.

I don't have enough of a background to provide you with, but I can tell you are contemplating it for 2 good reasons: 1. vacancy, 2. you have a heart.  

Also, take a look at Trulia’s crime map, as well as city-data.com - Trulia’s map for that intersection shows a mixed bag, but it also gives you what type of crime for the area (for example assault vs.

Matter of fact, the house that I'm contemplating buying is the house that I'm renting itself along with 3 other roommates (2 tenants and the landlord himself).