You will pay them and everything will then fall apart.

But don't let them know it.It amazes me how many of our members at MassRealEstate dot net have an Asset worth $300-500k Rent it for .5-1% of value and hardly pay attention to it, yet chase a tenth of a percent in CD rates;-)

I am just starting out with a STR and found that VRBO is not very specific if they are collecting the tax and paying it to the State as a marketplace facilitator or am I responsible for this tax collection and payment ?

yes create the addendum but realize the tenant who has been paying could ask to be reimbursed for these costs as well as not accept the addendum.

The tenants began pay rent on time, but then payments began coming in late, then half, then partial, then none.

I'll subto his existing mortgage and pay off the 120k.

Is it better to keep adding equity by doing work on the houses while I'm renting them then refinance to recover the initial down-payment to reinvest into another property or to pay down the heloc?

. - Inefficiency with payouts and administration will be compounded as the FAIR Plan has zero experience with a major pay out and lack infrastructure of assessors and technology to distribute the funds they don’t have.

I have done over 30k reservations and only had 1 instance of a guest causing above $10k in damage, so not sure how worth it is to pay for additional coverages. 

Also, how does one assess whether or not one can turn a profit after paying principal/interest, insurance, and taxes each month?