Michael,You have a few options for one you can get a personal loan up to $50K to consolidate highest payments lowest balances to help DTI.

This might help you get a bit of breathing room to address the bigger maintenance issues you mentioned, like the garage roof and leaning trees.It’s also important to find a support system, whether it’s other landlords who understand what you’re going through or a mentor who can offer advice and encouragement.

There are other options like resilient channel when hanging drywall etc. 

You can absolutely make rhe time limit what ever buyer and seller are comfortable with.If your trying to convince a seller to give you seller financing while you flip the house a shorter time may be more convincing than a longer one.You could also offer some of the profits from the flip to help seal the deal.

Then afterwards we make a plan based on potentially necessary renovations and decide together if I should make an offer.

At this point in time, I don't think selling would be my best option as I've spent a lot of money on capex items that I would not necessarily immediately get back from selling. 

In Louisville, neighborhoods like Germantown and Shelby Park offer similar opportunities.

I am almost ready to put in an offer for my first STR in Big Bear.

In this scenario, each member doesn’t actually own real estate, they own a business (that owns real estate).If that is the case you have two options: 1) The LLC performs the 1031 exchange and continues to achieve the goals of the managers through changes or details added to the operating agreement and subsequently consider dissolving the LLC. 2) You dissolve the LLC and reform as Tenants in Common *prior* to the sale of the property.

I have a nice down payment as was gonna offer a potential subject to if i paid their profits/ closing costs...but can you subject to a loan not in bad standing/ FHA?