Ik that here in Hawaii, there’s a few laws on STRs and I’ve been trying to understand but it’s difficult to decipher.

This can be very profitable purchase if you can fix whatever issue, but you are making it more difficult by setting a deadline.

Market might be competitive but there is angles to stand out depending on what you are comfortable and able to handle, such as waiving an appraisal contingency, limitng inspection rights and time frames, closing time frames, allowing seller to stay-post closing, taking on difficult tenants, buying properties that might need repairs, etc.

I know the 401 penalties are steep but my thoughts are if I can gain enough cash flow to leave my current career, do I really need to worry about whatever money is in there to draw from 20 years down the road?

I doubt if anyone is saying it's impossible for it to work but I feel it's difficult.

But those renting rooms in the area, can be difficult to deal with.

At the time, it never occurred to me that if you want to swindle people it is difficult and expensive to take legal action against a company that is incorporated in a different state than where they do business.

@Khaled El Dorry This strategy is know as a consolidation exchange, and like what @Adam Bartomeo said a single buyer might be difficult to find.

Yes if you're still employed with that company it can be difficult if not impossible to make 401k changes...

STR it will cost you big.this isn't a difficult job depending on the fridge location.