Am I on the right track?

@Mike Smithy  Looks like you are on the right track. 

But here are some really interesting numbers...Ok so this one doesn't look too bad but notice how much more the townhouses and condos dropped in prices over the last downturn.2007 peak to now isn't so good...Before the 2007 run up to now is better, but even then, apartment condos performed the worse (so best case scenario, you have the worse performing asset type, worse case scenario you had a terrible return), and that's assuming you had nothing go wrong with the condo (special assessment etc)But benchmarks don't even tell the whole story, because if you had a specific condo investment, and you tracked it's value overtime, benchmark prices isn't the right approach as it evolves overtime (benchmark price is the price of a typical property generated at each point in time).

It sounds like you're on the right track!

One other thing about investing in Jackson is that I find it hard to track the value of the house that I own there, which I bought in 2018 .

Among U.S. cities, counties or metro areas for which regular data is available, Maricopa County holds one of the highest eviction rates, at 16 filings per 100 renter households during the past year, according to Eviction Lab, a research group at Princeton University that tracks evictions in 35 U.S. cities and 10 states.

or Tracking my mileage is a hassle.

It'll be nice to use just one software, but I think it's better to use both Buildium and QuickBooks if you want to keep track of everything, likes your assets. 

I want to know how much skin they have in the game, the loan, and their track record.

I also had more confidence, more resources in terms of private lenders who were willing to lend to me because I now had a track record, and good contractors.By running my own marketing, I had access to a lot more opportunities and was able to start supplementing the cost of my acquisitions through wholesaling and the occassional flip which in turn expanded my network.