Welcome @Conner S..   Having

Outside of this site how many of you self-described coaches/mentors/guru’s have actually helped someone (other than friends or family) buy or sell an investment property where there wasn’t something in it for you?

Larger holes, I’ve used a can of spray foam then cement over that.

We own long term rentals in Rockford which is a great cashflow market, but w shave also been weighing our options to get a STR.

but I don't really want to risk going through a tough escrow with a novice buyer trying to shave me down with contingencies and unreasonable demands related to inspections... especially in a softening buyer's market. 

1/1's have been our slowest movers here in San Antonio lately, but they are still renting reasonably well.

As mentioned, normally any member of 20% or greater in the LLC will be asked by a lender to be an additional guarantor on any loan issued to the LLC.If any member(s) have a mid-FICO lower than the lender's required minimum, then the membership percentages can be adjusted to accommodate.

Seriously,you need to find a local contractor or building inspector to show you all of the actual problems that need repairs.If the plumbing and electrical haven't been upgraded in 100 years,change it all out immediately before they fail in the middle of winter.Make sure your HVAC is excellent as well.That roof probably needs tending to as well.Then you need repainting,spray foam insulation,flooring,etc.What fixtures is your competition for renters using in their homes?

So you have to think about how to hedge the bet as you have to play the game, and not try to time the peak or bottom, as your more likely to miss it than hit the mark.So tighten up your numbers, shave advertised rents a little or a lot, and ask them to give you the property for a dollar and buy you lunch, joking on the last two.

For tenants, I don't like that Section 8 tenants don't have the expendable income my other tenants seem to have, and mine tended to duct tape and spray foam everything and not tell you about it, even after extended conversations about calling and not repairing anything themselves.