Being that old of a house,I would also go after the major inspection items that are bound to come up. 

Is it in a downturn and loosing people now?

How do I go about increasing the rent without loosing the tenant and upsetting them?

Make sure you don't loose a tenant & an employee all at once.

Can you be lucky .. of course .. and on the flip side can you be unlucky enough to make you water down/shut off your passion of Real Estate .. absolutely Why i have said what i have said above  (handful of examples):1) You may have break in ownership 1/2/3 generations prior to existing seller (i had break in title  from 1949 or properties were in family for 3 generations but paper work wasn't done so NO ONE cant seller proprieties any more easily unless long drawn litigation takes place)2) You may have federal/other judgement associates with seller SSN which prohibits selling of any property owned by seller and not easy to find via a simple lien search (of yes... seen that a ton and loosing a great deal now for this)3)  Property could have utility/water/sewer/ground/air easement that  may not be easily found by county lien (almost lost quarter million for this reason)Having said above, re framing your question as how you can  delay spending money with Title company while looking for properties and/or getting into negotiating with seller where can you go to look up liens etc knowing you need need spend that money later. 

A good way to learn is if you loose out on a wholesale deal follow that deal and see what it sells for when it is done.

Along the way, I've discovered a few snags in my plan (a loose plan currently, but it getting refined as I learn). 

You will no longer be bound by the rules and regulations of a traditional IRA custodian, nor will you have to waste time waiting for a custodian's approval to make an investment transaction - since you have checkbook control you write the checks.

This is bound to happen and if you're already on a tight budget it's important to have that extra cash available.

Lets say they loose their belongings (furniture, clothing, electronics, kitchen wares, etc.) there would be coverage for them to be made whole.Good job requiring your tenants to have renter's insurance - it's as beneficial to them as it is to you as the investor!