Refi in year 5 to pay off balloon and keep the property longer; Or Sell it outright pay-off balloon and walk away with massive chunk of equity ($140K+)Return on Investment: Assuming you were cash flow positive for 5 years (99% certain), you turned your $23,800 investment into $140K equity position by year 5.

Based on your goals, experience level, and my assumption that high earning w-2s tend to be demanding of your time, I actually think that there are better ways for you to offset your w-2 income.

Yes, it is good area so I think it will appreciate, just we already bought with high price so not sure how much appreciated. 

Can you share any high level details about the nature of the trickiness so we can also help others learn on this thread?

I found a house that I think has potential - AirDNA is estimating 62K/year at 63% occupancy and $273 a night; however, I spoke with a Vacasa rep who thought those numbers were a little high.

Kitchen- range anti-tip missing, dishwasher high loop.

I honestly should have more money saved up considering my years of working full-time, however younger financial mistakes have been a painful lesson and I regret not purchasing a property sooner/younger.My most important and immediate goal right now is to purchase a property.I am in (what I perceive to be) a relatively high cost real estate area. 

But because of high prices and high rates most of the properties seem to be breakeven (at best), so this may be something to look into once rates decrease.

Hello Galen, I would highly suggest not trying to get super creative here and just form your own LLC, buy the property and put it in there, and write this one off as a win! 

And can expect somewhere around a 10% annual return.