I once rented a 5bed/3bath in two days, just a week before Christmas when the ground was covered with snow and ice.Sitting vacant in the winter increases the risk of frozen pipes or other expensive problems.

Home was nice 4 Bed 3Bth under $550K with a decent size lot/yard and it only required 5% down as a New primary.Now I am not sure how big of a home you need but as you can see $100K covers much more in a scenario like that one above. 

Will rent out the unit we’re leaving which covers about 65% of our new mortgage, if we pocketed it but that stays in the rental fund. 

I have a GC friend in PA trying to request 196k, as a “gap” to supplement whatever the HML cannot cover. 20% ROI, 6 months. 

You can only play games for so long.Chances are your next door neighbor is an IRS agent and turns you in when your tenants blocks their drive or some other random event disturbing your IRS neighbor.ADU catches fire and your insurance won't cover you, because it was an illegal and unpermitted structure.The city inspector told the last guy not to build or rent it, and is now pissed and wants to make an example of you and just red tags the whole property and no one can occupy for the next 1-2-3 years while you wait for a hearing.Then when you get the hearing, "staff" recommends you tear the whole structure down, and if you still want an ADU, you can apply for a permit and rebuild it.Your tenant quits paying rent and won't move out and you can't evict them, because there is no valid lease and they're just your "roommate".Probably a dozen other bad things can happen to you when you do stuff like this. 

We still owe roughly $900K on a 3% mortgage.We’re planning to retire abroad and are weighing two options:1.Sell the home – I already have a buyer lined up, so this would be a straightforward exit.2.Rent it out long-term (furnished) – While I don’t think the rent will fully cover the mortgage, it might come close.

However, vacancy means covering 100% of the expenses.Multifamily properties almost always generate higher cash flow due to multiple income streams, which also reduces the risk of vacancies.

We were always juggling who was on the phone.We had at most 2 employees on our payroll at one time, so if one called out sick there was a very good chance we needed to go in and cover.

Please let me know who you have worked with and why you like them (How many properties do they manage for you, how long have you worked with them, what you like about them etc.)When the unit is vacant, do they cover the cost for professional photography to rent it out again, or is that an additional fee? 

$2,698-$1600= $1098/mo would be your responsibilty and you said you could cover it all.