Nor would you be maximizing your return, albeit still getting a return, but there would be progression towards the goal.I would love to hear thoughts

Your goal, for you parents, should be to MAXIMIZE sale proceeds so they can afford the assisted living facility.

They may be trying to maximize their tax deductions. 

I have occasionally made purchases for the property on personal credit cards to maximize rewards points, or use credit instead of cash temporarily, etc. but I'd like to get everything completely separated because putting my income statements together is a mess if I don't stay on top of it (and programs like Stessa make it soooo easy if everything happening in a specific account is relevant to the reporting).Which cards/checking accounts/etc. have you liked the best?

Ideally you want to stay with the same airline and hotel chain to maximize these benefits.

I do have an LLC formed and set up, and I guess I’m just a bit confused on the best way to go about setting things up in order to maximize tax benefits, right offs, and other things such as that.

With this experience, I have a ton of knowledge about STRs and property performance that is fairly niche to my market.With this knowledge, I have been helping prospective investors / clients in choosing where and which properties to buy to maximize returns or meet their goals with their investments. 

Make sure the contractors understand they are responsible to remove snow to access their work.More cutting, prepping, etc. work will typically be done indoors so make sure you hire a contractor who likes to be clean and won’t turn the entire interior into a personal workshop/storage shed.Figure extra $$$ for temp enclosures and heat if you wish to do exterior painting, masonry, etc.It’s darker later in the AM and earlier in the evening so make sure you have a lot of good, temporary lighting so you can maximize the amount of time your guys are working when they are actually onsite.Planon missing a few days here and there due to a “snow day” when guys can’t make it to work due to a snow storm.

- I always make sure properties cash flow without STR and just maximize the return with STR.

But I need to fix the place up and maximize rent as soon as possible to make the purchase make financial sense.