If not, then the "smarter" way to keep that 66k is to owner finance until your rotation is up, come home and buy it during your next "home stay" via a VA loan. 

I have more of an idea of what I am doing but the financial strain has been hard, we have become really good at saving and lowering our expenses which will carry on going forward.

If you are not going to feel strained due to that $69.41/mo loss over the next year, I think it is better to hold onto it...again, provided you expect decent appreciation. 

@John Huynh - You'll almost always notice when you actually buy a house taxes are also rotated at a higher percentage typically 110% in Chicago. 

Quote from @Bryan Strain: So my girlfriend and I bought a house back in 2020 right when the Covid shut downs began.

I currently work a rotational W2 job (3 weeks on and 3 weeks off) and therefore do have a lot of time off and work on my real estate properties or learning, cold calling, DFD, etc.

Yes, infrastructure is strained slightly at the moment, but the influx of new $$ is causing new roads, hospitals, malls, condos, parks, etc... to be built.

It's not worth the strain on your marriage, and there are plenty other ways to make it in real estate.2.

The clientele was repeat guests, I had 6 rooms and a rotation of about 18 people.

One advantage I read about this is that it could encourage all tenants to take better care of the shared spaces or everyone could be penalized.How should I handle this though if tenants are moving out at different times and consistently rotating?