Covering most of the routine maintenance items here. 

Due to item 1, adding an ADU can require years to start achieving any return (once the accumulated cash flow recovers the initial negative position).4) Adding an ADU is a slow process.

Or should I just not worry about that and go with whichever has the lower payment knowing my goals are to lower carrying costs and I'm going to pay off the principal when I sell.

We’ve got to separate this type of loss from those in which the 5 items listed above weren’t followed. 

., as Bad habits in one area typically carry over to other areas, and will land you a poor Tenant (or co-signer) choice.

Close costs/carry on both sides will be around $17k.

Chip and Jo cannot carry Waco on their back forever.

From page 730 (emphasis mine): "All non-business tax deductions and exemptions that were temporarily suspended by the 2017 tax bill should be permanently repealed, including the bicyclecommuting expense exclusion, non-military moving expense deductions, and the miscellaneous itemized deductions.23 The individual state and local tax deduction, which was temporarily capped at $10,000, should be fully repealed.

I am also looking for information regarding fee structures, and what item's that should be and should not be included in the management fee calculation. 

Water heater 12 years to replacement (may need some service before replacement).Recognize many cap ex items are years away.