(I personally did this) I would say though that in the worst-case scenarios that you mention of loss of job and such, I view it as more helpful to have someone by your side helping you construct a plan through it who has been through hundreds of those situations before helping clients.

For seasonality, I take into account holidays and local events that might drive demand.I'd be happy to connect for more ideas! 

Additionally, would love to hear how others manage multiple listings with the help of others.

It sat on the market and dropped in price a couple more times at which point we decided to make a new offer.

This would help you get going.You might be able to make these a  little nicer and force appreciation and a little higher rent.Either way rents will go up over time and the mortgage with remain constant.Maybe even make one unit a STR which could see higher income.I'd be ok with break even or a little bit negative on a Quad given you have 4 properties in one.If you're only breaking even you still have depreciation and other tax write off to help you out.I usually make people 3 offers.

Visit with people there and you'll get a more detailed look at things from people actively working in the areas.

It seems more your fault for choosing the "lying" contractors from the tenants point of view, if you ask them to pay up, I'm sure they would.

Thank you for any help or information!  

There’s no single right answer to every situation, but the more you educate yourself and build your network, the more confident you'll become.Lastly, don’t hesitate to ask questions here, no matter how small they seem.

Repayment options can be more flexible like in my case I do everything on accrual this really helps flippers when they dont have to make monthly payments.