@Ryan Sargent We have 4 vacation rentals thats located approx. 1,000 ft from the beach but you still have to cross a low traffic 4 lane road (2 lanes each way) so it takes 5-6 minutes to walk. 2-3 minutes for a bike ride which we do provide as well to make the trip easier for some.

(I've heard many a loan officer be taken for a ride this way).

With the historically low interest rates we're seeing now and the potential turbulence that may come in the next couple years, savvy investors are making sure they can ride out any potential storms without having to refinance at a time when the loan market is way less favorable.Best advice is to get a good commercial and residential lender (likely different people) in each market you're looking at and pick their brains about what's possible right now.

It's nice just sitting back and collecting interest instead of running around meeting with sellers, contractors, title companies, etc.Yes i found this a very natural progression for many investors.. almost all start out with rentals.. and over the years they just burn out of them.. but want to stay in real estate understand real estate and then morph to the debt side instead of the equity side.. but believe me when a loan goes bad you do have your work cut out for you.. and you can for sure lose money.. 

And you're way too young to forgo interest investment compounding so I'd keep contributing enough to retirement accounts to get the match and let it ride.

You get the best of both worlds, cheaper cashflow property deals and walking distance to Miller Park tailgating fun or short ride to the downtown.I had the same idea, moved to Milwaukee post college, rented cheap place downtown for 1 year and then bought my first duplex in 2004 in West Allis (Six Points neighborhood - northeast West Allis).  

Good luck and enjoy the ride!

😊keep in mind just becasue they are underwater does not mean they cant make thier mortgage payment and will simply ride it out.. and if they are underwater.. short sales take forever .. interest rates are so low even if they pay more the owner occ in many cases is less than rent.. so why would they sell only to rent for higher dollars ???  

Learn to ride a bike on a flat surface before attempting a downhill backflip.

Perhaps a second gig or ride-sharing if you have the time , but uprooting yourself just doesn’t seem worth it.