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

You can find online mortgage calculators that allow you to play around and see what happens if you do an extra payment or increase your payments.

Adding in the layer of not being on the loan but holding title just sounds like it will eventually lead to problems like OP experienced.

I know it seems like a tough task, but can you spend a few more months or a year while you continue to learn to really tighten the budget or find ways to earn a little extra to start from a stronger position?

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

Even simple extras like local guidebooks or maps can make a big difference.

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?

Some companies might charge extra for maintenance coordination or inspections.

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

Shouldn't be any extra taxes involved.