The only factor that I should clarify is that I would use cash on hand to add that additional bedroom (and remove an undesirable tenant), which I hope would add something to that valuation — I've read the 11% range is not unreasonable (*please comment on this, anyone who's done this before).

Clear as mud what the best option is ... :)I would pass as a buy and hold......

But it only happened because people who are more experienced and better than me knew that I'm looking and want to help. if you want to be in the game stop spinning your wheels in the mud and get out and push. 

It's hard because sometimes  a paint job requires tons of extra spackling / mudding, other times none, sometimes it's same color so 1 coat, sometimes no trim, or one coat. 

But the meter right next to my meter is broken and mud is caked on the gauge's face.

i just encountered popcornesk wall texture and just mudded over it to make it smooth.

In my opinion, drywall mudding is more of a skill than plumbing, but the field is less regulated, and more accessible, so the labor cost is less.It's a good idea to try out doing some jobs yourself as you'll learn crucial skills useful for when you pay people to do it in the future.

If there's an undesirable lot or funky house they can't move, they'll negotiate on it much easier than an owner occupant who has an unrealistic expectation and can't afford to discount.

Evaluate what traits you consider to be a generally accepted as desirable and undesirable and write them down and do the scoring of 1-4 for it as well. 

If this area is less desirable, you will need to use comps only in the same undesirable area.