Hey @Matthew Samson, regarding "figuring out the financials" for 0-5 small properties, you can do this easily yourself just using excel or another free method.

It hasn’t traded since 2008. 

So the enemy method is the way to get a good idea.Check AirBNB and VRBO and see what similar properties are doing in the area.Also, Louisville recently tightened up the rules around STRs so check with the city and make sure you are good to go for a particular property.

Income from a trade or business where a taxpayer doesn’t materially participate.2.

Register for guru courses that cover the topics of the BRRR method and subto financing2.

Preferably, you or the seller have a method that can be set to autopay to make both of your lives easier.Hope it helps!

I would use AirDNA and "the enemy method" to see the most successful STRs in the area.

If by real estate business you’re implying you have little or no money to invest but are contemplating using one of the guru inspired methods (subject to, “wholesaling” , fix n flip) to create cash flow, I’d encourage you to do research on the true success/failure rate of people who engage in these endeavors, the amount of money the successful operators spend monthly on marketing, and the real time commitment and knowledge and experience necessary for success.  

@Maxwell Hinesshort term - BRRRR method, for example.buy with cash or hard money, rehab with HELOC money, then refinance and pay it all back.you never want a HELOC as part of a long term situation.

An owner trades the predictability of a low Flat Fee (which is typically charged every month whether property vacant or occupied, tenant paying or not), for less PMC alignment with the owner's interests.