Talk me out of it — first-time STR buyer, self-managing from a distance in Northeast

I host from across the country. The best advice I can give you when you manage from a distance is to stay in the house for awhile yourself, and go through everything, getting the house in top condition before guests stay. Take showers or baths and use the toilets in all of the bathrooms to see if everything works well and the tubs drain well. Replace or repair everything that will likely give you problems with guests over time. That means changing any toilet guts that don't look new, cleaning out all P-traps under the sinks and tubs, replacing any faucets that don't look new, any water valves that look like they're getting older (including the clothes washer valve and the hoses to it). Change all light bulbs to LEDs if they're not already, change all smoke and CO detectors to 10 year battery ones so you don't get a call about a beeping smoke detector. Make sure the heat pumps or AC and heaters are in good condition and serviced every year. Take a look at the water heater and make sure it's not too old and that it can handle the number of showers of your guests without running out of hot water. Don't pay for a home warranty for an STR - they take too long to repair things. You need your appliances repaired ASAP, so you'll need to pay an individual repair person.

Because I keep the house in top shape, I get very few complaints. In the 4+ years that I've rented, I've never had a guest call in the middle of the night.

The guests staying in the master bedroom are usually the bookers, so cater to them.  Make sure that room has black out shades if needed and everything is how you'd want things at home.   

I'm sure you know that you'll want to use smart locks, smart thermostats (put temp restrictions on it), video doorbell or cameras, and possibly a water heater alarm that detects leaks.  

I sleep 9 in a beach area, and haven't had any problems with parties. Mine are mostly extended family groups, but I have had groups of friends and they've all been good. I put in my description that this is a family rental, the HOA has "quiet hours" and we don't allow parties or events.

Just starting out, for handymen or other recommendations, ask your realtor.  They will often have multiple contractors they like because their clients always need remodeling when they buy through them.  My realtor recommended a flooring guy for me, and because of that recommendation, he got me on his schedule much faster than he would have without that.  You should also join Facebook groups for your town and ask for recommendations.  I've found a good electrician, appliance repair person, and furniture refinisher that way.  

For cleaners, I first asked my realtor who gave me some names.  They were all too busy to take me on, but one recommended a friend who was starting her own business, and she is great.  Beside asking on FB groups, you could also look at neighboring STRs that get great reviews for cleanliness, and go there on a check out day when their cleaners are there, and ask them if they're taking new clients.  I don't decide what to pay the cleaner, she told me what she charged and I accepted.  It's not hourly, it's per clean.  Remember they have driving time and gas, and they need to clean within a small window on turnover days, so if you want to keep a great cleaner, you can't micromanage them.  I am not passing the entire cost to guests.  My cleaners cost $330 a turn, I charge the guest $270, and I up the nightly rate a bit to cover it.  My cleaners come as a crew of 2 to 4 people, which is better than having a single person with no one to cover them in case of sickness or vacations. Your cleaner is the most important person to you.  Cleanliness is the most important thing with STRs.  Your cleaner can be your boots on the ground if you arrange that with them.  

I am in a beach area where there isn't much demand in the off-season.  I use PriceLabs, but they were too high in the winter and I got almost no bookings.  So I dropped prices way down, and my bookings picked up.  You have to think about heating costs for your big house, and what your bottom price would be to make it worth that cost plus the wear and tear that guests cause.  You could try listing on Furnished Finders for a medium term rental in the off season.  It didn't work for me, but maybe it will for you in your area.  

If STRs were ever restricted in my area, I would not be able to break even using the house as an MTR or LTR, so I would sell it.  Real estate is always going up here and mine has appreciated, so I would make money on it.