Hi @Alex Juarez. Some thoughts...
1. Utilities - For water you are going to have to find the utility district that serves your home. This is always fun...not to hard to find who, as that can be found on the county tax site. But finding a phone number or website can be challenging. Most of the water utility districts are pretty old school and you may literally need to drive there and bring your closing documents. Your tenant will need to do the same once they have a signed lease with you. As for electricity, I used to always just call my preferred provider (I always used Reliant)...tell them it's a rental and sign-up for a basic plan. If you are doing renovations and have alot of contractors you can get a plan that offers lower rates during the day (when they are working). But regardless, you will not have the plan long so it doesn't matter too much. Ask the REP (retail energy provider) to set you up with a CSA (continuous service agreement) so that when the tenant moves out it will roll back into your name (you don't want to lose power and have to pay re-connection fees, etc.). You shouldn't need to worry about the contract too much as you are not penalized for a "move-in". You are only charged penalties when you switch providers before your contract expires. No need to look for month-to-month plans.
2. Advertisement - Cozy syndicates to several sites including Realtor.com, Hotpads, etc. It's been awhile since I used it, but don't recall they syndicated to Zillow. But you can just set that up manually if needed. Where you advertise depends on what target market you are trying to reach. The most traction I ever got in my single family homes was through Facebook. However, that was also where I got the most tire kickers and flaky people. Never had much luck with Craigslist...but probably doesn't hurt. The real question is whether you want to use a real estate agent and list it in the MLS. My wife is a realtor and always gave me a hard time about NOT using an agent. Even though I would save on her commission I never wanted to pay the buyer's agent. But you have to weigh the amount of opportunity cost if you are sitting on your property for 3-4 months trying to lease it on your own vs paying a commission. There are some flat fee listing services and you can offer whatever you want. Just know that agents are likely to show properties where they can actually make a buck. Personally, I did a bit of both. When I had properties in a hot area at the peak of the season I marketed them on my own. When it was the slow season (yes, you are in it) I would sometimes list it in the MLS and pay the commission to get it rented faster.
3. Timing - No one says a lease has to be an even 12 or 6 months. I would sometimes create 10, 14, 15 month leases, etc. to try and get the end date within peak season. Some tenants may not go for it but just don't try to thread the needle...even if you can get between Mar-Sep you are doing ok. You just don't want to be in the same cycle every year of having turnover in Jan/Feb. But you also don't have to do it all with one tenant. For example, if your property gets leased in Feb and you can squeeze a 13-14 month lease...and then if you get turnover you do the same with the next tenant....you will get to where you want to be fairly quickly.
4. Rent Collection - When I first started I had tenants mailing checks and even once had a tenant put a check under my doormat at 11:59 pm (NEVER have tenants come to your home...it was a huge rookie mistake...but live and learn). Once I found out about Cozy I never looked back. All my tenants were on it and the entire process was automated and seamless....from advertisement, applications, background checks, leasing, and rent collection. Tenants liked it too! They appreciated being able to set reminders and automatically debit their accounts.
I hope this helps! I've since moved on to multifamily and third-party property management but really valued all the things I learned by self-managing my SF rentals. Best of luck!
Tony