Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

I have one I have drafted up but would love to compare against others.What are some items you always included in your MTR rental agreements?

I am curious though, in hindsight, how does an investment in STR in Hawaii in 2012 would compare with other markets over this period of time despite all the regulation headwinds?

The 2nd person really liked the house and even mentioned how nice the rehab was, relative to comparables they have seen.

You could also get a couple different agents in the area to get you good comps on what to sell it for and compare on what they say the out price can be. 

Whether you should take a retirement distribution or not depends on several factors1) How much do you value the freedom/flexibility to ues the money NOW compared to when you are 60 years old.2) What type of return can you get having cash vs investing in an IRA / SDIRA.If you can make a 1% - 2% better annual return in your personal name, it may make sense as the added return will pay for the penalties over a couple of years.I personally cashed out of my retirement account back in 2016 and it was the best decision I made.

It probably won't come close to $150K.Run the numbers if you put the profits into a savings account paying 5% interest and see how that compares

Any kind of non QM financing will have higher closing costs compared to conventional.

Confirm that the warranty applies to the type of property you own and consider whether the annual cost and service call fees make sense compared to just handling repairs yourself or using your own trusted contractors.

HUD and Agency financing is another beast compared to conventional or non-bank lending (Secondary Market).