I believe me as a licensed real estate agent that is classified as “steering,” requiring a consumer to use a particular vendor.

The best strategy is to get a lender that will use your non taxable income, keep a high credit score, and keep your personal consumer debt down.

Single familyPros - available at every price point - easy to understand - comps are relatively easy to determine - numerous exit strategies available - less complex to rehab- less complex to BRRRR- better likelihood of natural appreciation - Less turnover - Fewer tenant headaches- Tenants pick up most/all of property expenses (also, no common areas)- Tenant more involved in upkeep- More financing optionsCons - a lot of competition (regular buyers, other investors)- inherently slower to scale than multi familyMulti familyPros- scale up is built in - more cash flow vs amount invested?

With utilities the company would make sure they had a baseline of costs to estimate your consumption (in this example electric bills for the previous two years) and then if you consumed less than the estimate they actually sent you a check at the end of the year and if you had consumed more than the estimate you would just owe the difference.

The investor who wants out of real estate, to invest in something less active, time consuming or less risky, or to spend the proceeds on something else, does not accomplish his goals with a 1031 exchange.

I would look on Vrbo and airbnb at other similar properties in your area to see if this is realistic.Then you have some money for maintenance and upkeep, consumables etc.I would put all this in Excel and see how the numbers look.Then you can easily adjust numbers to look at options like a remodel or full gut of the house.You mentioned a pool so you'll want to have a professional pool company maintain your pool to limit your liability on the pool chemicals being off and causing a problem for someone.

The time and $ cost for using an LLC is worth it to me to keep my personal name and SSN in fewer places. 

Things are generally less congested with fewer traffic issues.If you're looking for affordable MFRs, my favorite places to look are the west side of Brockton, Middleboro, Plymouth, Wareham, Pembroke, Kingston and Marshfield.I ran the numbers recently and found that for what you'll pay for a 3-plex in Boston, you can buy 2 or 3 in Plymouth County.

I have hundreds of rentals with them and probably have to unclog about a dozen a year and replace even fewer. 

With boarder income, there are fewer loan programs that will count that income.