Finding a deal on that list is challenging. 

We often give owners advice before the turnover letting them know that if we turned over the tenant, how we could improve the property, at what cost, and what the rents would improve to.

If I finance the rebuild then the 1031 exchange presents some challenges (I will need to land a property that cash flows or breakeven so that I can get the loan for my rebuild, or banks will count that debt against me).

This market is challenging. 

Their biggest challenge was finding a reliable cleaning crew, but once they built a team, everything ran smoothly.Let me share another example.

The Cape also in my opinion is oversaturated with STR's so it's challenging to find a base number of how your property will perform. 

The best you can do research your market, improve personal budgeting, improve credit, and get your dollars working for you.

Sometimes you have to challenge the SOW and determine if everything really needs to be done in order to attract qualified tenants.

Before listing it on an STR platform, I need to make some improvements to my current home.How can I maximize tax write-offs for these improvements?

Quote from @Nathan Gesner: Buying a house is straightforward; managing it can be a whole different challenge.