I'm looking at a 4 unit off market deal in East Boston now that might make sense from a condo conversion perspective. 

Does that make more sense?

If something for example costs 2x as much but last 4x as long....... it would make more sense to buy the more expensive item less often...Both these are even more critical when dealing with trades/people.

If that does not make sense, then the option is to terminate the 401(k) and roll the assets to a suitable IRA.Best to discuss with your 401(k) plan provider and CPA.

I would expect for a 160K house the rent would be around 1100 not 2100, however if you did the full rehab and the property is really 360K then 2100 would make more sense. 

The extra income just made sense to me since I didnt have a family and had some extra rooms.

I hope this makes sense, and please feel free to PM me if you would like a more specific answer or if you just have further questions.

Does a hard money loan make more sense (they scare me)?

It's much less common to pay closing costs out of pocket for a refinance than for a purchase.

If buying a property with cash outright, would it not make more sense to write and sell your own note on that property instead of doing a conventional cash out refinance?