Hey @Morgan Iacolucci, @Pat Aboukhaled has some great insights here, and I really agree about locking down that buy-back clause right away.

Completely agree with @Arianne L. - not having a strong or deep 'why'.  

As for vehicle vs RE, I agree this was a vehicle but the peace of mind was unrelated. 

Actually, seems like you AGREE with me

I even calculated and mentioned that the costs would total $15,700 for the project which was agreed upon.I had also told the PM that if any extra costs come up to let me know so I can watch the numbers.

The real estate investing industry uses "Classes" to rank property performance risk, but there's NO agreed upon industry model:(Here's what we use for our Metro Detroit market:Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

At the same time, people who invest over the very long term seem to agree that focusing on the thing you know best results in the highest returns over time. 

I would have to agree with this - appraisals are no exemption to the general inflation/rising costs of the past few year s- $750 is hardly outrageous and investing in non-warrantable condos and with HOA restrictions is always going to have a risk for hiccups

I agree with Collin.The Smokies do have a lot of competition, so you need to have a view, decent location, good to great amenities etc to stand out.We have a 6-bedroom cabin there, but I imagine a 3 to 4 bedroom would be in the sweet spot of not too big or not too small.

It's a great strategy but I agree with @Jack Seiden, having roommates at 30 isn't ideal.