A few points.By way of background, we have a two-family home in Weston, which is about 15 mins from Okemo, 15 from Bromley, 10 from Magic and 25 from Stratton.

Things I've got down to minimal effort or fully automated: * Rent, security deposit, and fee collection* Basic accounting and tax packet creation* Listing vacancies* Lease signing* Applications, credit, and background checksThings I'm still dealing with directly ad-hoc or don't have a well defined process or solution in place for:* Requests and communication with tenants* Finding and coordinating service providers for maintenance and repair work* Scheduling showings and getting prospective tenants to make their appointments* Tenant turnover for move in and out* Keeping up with legal changes and lease template updates* Setting rent amounts* Lease enforcement - tenants are responsible for things like yardwork, routinely get letters from the city about weeds / tall grass, etc.Questions for the group:* What am I missing if I were to make out a checklist of an "automated property"?

Never EVER accept or agree to accept any tenant without properly conducting all points of discovery and creditworthiness [ability to pay], background [character] data [patterns of behavior in past residences], etc.

You can't be pushy, because some appraisers are grateful that you are basically doing their work for them, and others think they know better, so you need to stay in the background with the latter.All that being said, I have heard from several of my realtor friends lately that they are seeing far more issues with appraisals coming in short.  

I have a background as residential landlord.

Since I lack a legal background, I don't want to risk handling it myself, especially for our first rental.

I know you have a finance background and to each their own, but leveraging debt is a much faster way. 

With a background in Engineering, I’ve developed a passion for real estate investment.

But if it is a couple of months situation I would need to know who it is and have them background checked.

I run a vacation rental company with about 50 homes under management, but I also have a nonprofit management background.