House needs some Interior Cosmetic Work, Wood Fence Repairs and some Plumbing Work.I want to turn and run, but I recently heard where there is a Problem, there is Opportunity.I thought this might be an interesting Case Study.Thanks for the Ideas.If the situation is as dire as you suggest, there are other bills he hasn't paid and there are likely liens on the property.

There are Class A industrial projects underway and the development of a large retailer.

The wall street journal published a piece suggesting home prices are overprice and will likely fall. 

It gives me another exit strategy by having the option to sell off individual properties to retail buyers if needed.

I suggest you form an answer for each, @Jonathan Warner.

Regardless of how a certain asset class is doing, an investor like yourself can ALWAYS find a good deal in any type of property.Now, my general suggestion for all of my CFO clients is the gradually move up the unit spectrum/asset type as you build up your portfolio.

So I would suggest keeping your STR property geographically close and doing as much as possible to keep your profit% high as possible.As far as the actual house you use, I would just say - be honest, be fair and strive for the best area, most amenities, cleanest house, best communication, and any other extras you can get.

Used your HELOC to fund the down payment on a second property if the right opportunity presents, otherwise those returns wouldn’t be juicy enough for me to take on more debt for the sake of scaling if you’re buying at retail. 

You wouldn't need to keep an eye on other investments, just focus on the one and maximize your cashflow.If I can make a suggestion though...I might be wrong, but I don't think you started househacking to take the simple route. 

That person is responsible for anyone one else that comes into contact with your property.I suggest using a service like Mayistay.