When you are dealing with entities I generally lean toward using an agent trust to own my LLCs or Series LLCs.

Also leaning towards a hard no, but checking with my insurance company; I have a feeling its a no from them too.

Super convenient. 

Very convenient and handy for me in properties I self managed.

., for your relatives or a partner's), then a 2F might be a good choice because you can rent it now but potentially convert it to personal use later.Since you're only 20 and may not be thinking about taking care of your or a partner's relatives at this point, I lean slightly toward a 3F being a better option for you, but it's really a personal decision and if you find a good 2F close to you (or in an area you really like) then I'd say go for it.

I'm also looking at whether a parking lot lean-to could fit in the parking lot to see if I could gain an extra ~$40 per month from people who would appreciate covered parking for their vehicles.

Any and all advice, and info will be very much appreciated.I do hope to meet & connect with local REI's in the Missoula, Montana area (where I am) and any investors anywhere that leans more towards creative investing over flipping & fixing, and wholesaling.Thank you very much!

In my opinion what you're feeling is very natural which is why you lean on the math or connections with more experience to help level out the emotional roller coaster ride which is real estate.

I’m not talking about rehab budgets, but could there be hidden lean?

I was leaning more towards buying.