@Carlos Martinez - Are you able to provide a cost estimate for the roof and/or the increased cost of the premiums?

I only have Long Term Rentals - for me it would be way too much work to do STR with a W2 job, unless I pay a property manager but I'm considering doing an MTR if add an ADU to my LTR (downstairs could be a studio apartment if add a kitchenette), haven't gotten any estimates yet. 

Also, good point about it potentially being more than the estimated 3 days once they get in there, I hope not.With all that being said, I am trying to be as unbiased and remove our “history” so to speak with these tenants regarding our decision for reimbursement, and making it purely about what is legally required and appropriate given the repair.

Having trouble analyzing this deal as there are so many variables and I do not have the experiencing analyzing deals to make me feel comfortable taking the risk.Purchase price of the land would be $250,000 not including closing cost or fees, and construction for a new 3/2 home with an attached 1/1 ADU is estimated to cost around $300,000 - $400,000 finished.

Cap Rate (Capitalization Rate): Used by investors to estimate the return on an investment property based on the property’s net operating income (NOI) and its purchase price or market value.

Here are the numbers:Purchase - $70KRehab  - $50KARV - $180KCash out refinance - will get 100% of my investment back or pocket up to $15KProblem - I am estimating that my monthly cash flow will be about $100 a month.

If you could work it into a combination STR/MTR and rent mid-term to people working in the area for the down months, the market could work, but aside from that I don't see a ton of value in that market for the prices you have to pay, you basically have to make a years worth of expenses in a 4-5 month span.I don't have specific knowledge of any of the other markets on the list, but based on this one it seems like not much analysis went in to any of these properties and its strictly based on a rough estimates of revenue.

Rental estimates for each of these apartments is $700-$900 per month.

However, failing to pay the tax could result in a lien against my company, complicating the approval process for a mortgage and incurring an estimated $10K in penalties. 

Now the property is about $300,000 as per Redfin estimate and I still owe about $150,000 with the bank on this loan.