Logically I am thinking 30-year mortgage as I intend to sell the property within 4 years, not enough time to see a difference in the interest payment (graduation of college) but am not against holding if rents keep sky rocketing to what can be a comfortable COC once I move out. 

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.

If she has family/friends I would enroll them into helping find charties/churches that may help our or other places for her to live where she might be more comfortable, with said family and friends for example VS alone.While it wasn't covid, we have done this a number of times with families and local programs. 

Having access to talk everyday to investors, attend calls where I can talk about my deal and run my numbers makes me so much more comfortable now.

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.