@Travis TimmonsI had the same reaction as you did, but I held off on posting since I don't yet invest in STRs (I'm all LTR so far, and looking into my first MTR).Buying an STR "to offset income" makes me nervous as well...

I suspect it will be well used and have high maintenance costs.Software: office of google office, asana, possibly quickbooks (i would normally not suggest for a single rental, but the rent by room compounds things).  

If there are lease violations, mention them-you not having a key to access the unit WITH proper notice or in case of emergency is one of them.I'd also tell the tenant that they are clearly not happy there, so finding a new place is in their best interest as well and as they have several months, they should have lots of options.

We've utilized the VA loan for our current home, and this strategy has worked well so far.

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The deal is risky unless you know the market well, have experience executing this strategy, and have accounted for the quality of the asset and tenant. 

Looking to add some unique features as well, but some of the draws would be a hottub and stocked pond to fish from.

Many of the loans we see also are not well underwritten and properties are at 125%+LTV2.

– Considering Class A properties with established tenants• Less focus on appreciation – Prioritizing income stability over potential future gains Current Opportunity: I’m evaluating a retail property in downtown Portland with:• >80% occupancy, most tenants in place for 10+ years• Decent cap rate (6-7%), NNN lease• Well-maintained, high-quality building, with existing HOA which will take care of maintenance. 

Patricia- If you are looking into professional management, one of the first questions I would ask is about their cancelation policies as well as reading their reviews.