First unit lease is up for renewal on 10/31/2024 and has a good long term tenant.

I was actually a student at the university there not too long ago, part of the wine program.

We've done this many times where you purchase a property at a discount with short-term financing/bridge loan, rehab it to increase the value, rent it out and then when you refinance it with long term financing, you (hopefully) get some money back.

I know if card X is charged, it's the cleaner at my North Carolina short term rental, for example. 

Frankly, I wouldn't feel comfortable owning a condo long term due to rising HOA costs and major assessments.

If, however, that means you own more real estate in locations that you like, you get the magic of leverage + appreciation that results in a better long term return. 

Before you start asking any questions you need to get an idea of what you qualify for in terms of financing.

What recommendations do you have in terms of what to take a look at/action items after 1 year? 

Hello, long-time reader of BP, first-time poster!

This is common in my area/Colorado in general especially the ski towns that still allow short term rentals.