Your husband does not qualify for REPS anyway, but you do not need REPS to benefit from the so-called STR loophole.More importantly, STRs typically create large tax losses in the first year only.Most importantly, taxes are never a good reason to choose a poorly performing investment, IMHO.Read this post: https://www.biggerpockets.com/forums/51/topics/1122635-the-s... 

At that point, it's worth researching and finding a solution that better meets your needs. 

Typical California BS!.

Is the maintenance of the pool worth the hastle? 

No signing expensive leases that you personally guarantee typically. 

I work for BiggerPockets so of course biased but I think the Pro membership is more than worth it.

For example, is $150/month enough to be worth it with potential maintenance costs? 

Alternatively, would this work as a typical STR?

I am a realtor in Fort Worth & investor myself.I have 1 SFR via house hack.

It's worth noting on the STR side, CT is not exactly the AirBnB capital of the world.