I am happy to help, but let me tell you this story first (it's one of many similar ones in regard to moderation of groups):When I was still at eXp, I offered to moderate their Workplace forum The Watercooler because it was full of spam.

I am planning to expand and in a near future add more houses to my portfolio.

You're monthly allocation of "roof future cost" doesn't happen when you want it to, it'll rear it's ugly head when it wants to.

If not feasible, consider increasing rent, reducing purchase price, incorporating future benefits, or targeting multifamily properties.

@Rocky Gibson how much are you needing for your future development projects?

In the future if you plan to continue to invest in STRs, would encourage other areas - shoot me a DM and happy to walk you through where I'm seeing the most friendly regulations and best cash flow. 

Treat it as a business, this is not your money, it is your future... treat it as such. 

I'm looking forward to shifting my portfolio in the future to longer term tenants. 

@Sendil Thangavelu you really need to hire a professional property manager or real estate attorney to help direct you in the right direction from now and the future

Agree that no insurance will cover future increases in cost of monthly or yearly HOA assessments (dues).