For example, this can be adding square footage, adding an extra unit, or adding a pool in a STR market/luxury market.  

Purchase price: $82,077 Cash invested: $50,000 Sale price: $275,000 Fix & Flip mobile home with extra lot.

We closed the LLC because it was not giving us protection since the properties and mortgages are under our names instead of the LLC, so it was extra work and cost for no benefitQuestions:1-I assume we need to issue 1099 for these contractors even though we are not incorporated, right?

Is it worth to invest and learn from their program in order to start my co-hosing STR side business just to get some extra money monthly?

Otherwise perhaps your winter people will pay $500 extra if your cap is $500 and that is not what your competitors will be doing. 

It almost feels like they make it difficult on purpose so they get extra revenue on late fees.

15 - 20 year hold time.The rental investment calculators show that the four $300k properties would have a lot more equity in the future and many times the cash flow after a few years, but does the extra maintenance, management time and expense, etc. outweigh the numbers?

It 12 years, assuming you make no extra payments, you'll have a paid off condo that cash flows a lot better. 

It shows you are serious and willing to go the extra miles to make it work.

We all know what goes on in bathrooms and what kind of extra care they need.