People who don't actually own property in Detroit 2.

You could structure the deal with seller financing to bridge the gap.Possible offer structure:-Purchase Price: $170K - closer to actual value-Down Payment: Low or zero down to conserve cash-Interest Rate: 3%-5% - or better yet, 0% if the seller will agree-Monthly Payments: Interest-only or deferred until the sale-Balloon Payment: Full payoff in two years when you sellIf he wants $200K, you can still make an offer of:-$170K purchase price + $30K as a second lien due at closing-Seller carries $170K at a low interest rateHe would feel closer to his number, but you still keep within reasonable investment limits.2.

in either case, does anyone have tips as to go about the actual pitch?

There’s also a good mix of duplexes, triplexes, and quads, so you’ve got options for a solid house hack.House hacking is actually how I got into real estate—I’ve done two house hacks with duplexes here in Chattanooga, and it’s been a game changer.

The SPB and TI areas are actually generally not STR friendly and have 30 night minimums for single family residences. 

If you find an actual property that looks like a homerun and would warrant a HELOC, then you can go for it without reservation.

My business partner and I actually own a portfolio of STR's in the area, so if you wanted some insight on that business I'm happy to share as well!

We’re actually in Tucson this week so I may even have some availability to meet up. 

I can find the deals through certain websites and other resources, but i hav barely a clue on how to actually pull the comps.

I actually had your underlying question in mind.