If you spend a couple years of cashflow on a new roof, that means you should be free and clear for a couple decades.

Quote from @Tessa Tsui: You claim to have read those articles before, but you are using the wrong terminology and asking a question that is clearly answered by the resources Russell provided.

These bushes are clearly too close to the house.

The arguments for FHA versus conventional are fine and all, but one thing to be absolutely clear on is that Fannie/Freddie nor any other agency does NOT lend to entities. 

I’ve had the house for 6 month and I feel like there’s so much deferred maintenance that I can’t keep up, should I cut my losses and sell the house?

You can go over cost vs time all you want but at the end of the day, for me anyways... doing the stamp licking, printing cutting etc... just sucked big time and I'd be a very happy man if I never did it again. 

By documenting everything, both parties have a clear record, which can be invaluable if any issues arise later.

A well written management contract should clearly spell out what is expected of both the PMC and the owner, to PROTECT both and avoid misunderstandings.

Once you know your goals and investing time horizon, the optimal choice will appear much more clear! 

Some extend their contracts and will want to extend their leases, others may have their contracts cut short abruptly.