If you would like to jump on a call soon I'd be happy to share my local insights with you.

I'd also recommend joining a local Indianapolis based REIA asap. the REIA will provide a group of investors who could get you some contractor recommends if you decide to GC the prop yourself.You said it "needs a little work done" but budgeted $50k so those two things kind of contradict unless the home is a larger home...just curious, what's "a little work", if you haven't had an inspection yet and don't feel comfortable evaluating the costs on your own?

If that's not an option than you'll have to close and serve notice yourself and abide by your local laws.

There are some active Jackson locals on here, I'd connect with them and ask them about this property. 

I'm only guessing but based on what some of the local project managers were saying is that a typical family of four that was paying for a three bedroom cabin decided they could get by with a one or two bedroom with a loft or a pullout sofa so the demand from the larger ones went up. 

Congrats on getting an STR as well, my partner and I specialize in STR and flip investments in the area so we have a lot of local connections that could be useful for you. 

I’ve seen a couple of the local guys switch their strategy to one- and two-beds.

Companies like PolicyGenius do an excellent job selling personal lines coverage (property/casualty and life, mainly) more easily (and maybe more cheaply) than your local State Farm agent.

Hi @Avi Manthe being a local milwaukee real estate investor here are some organizations that are worth checking out to grow your network for hard money, contractors, etc. 

Check with some local banks in the area and tell them your plan.