I would look at the cost and ask your team if the extra expense will be made up on a higher sales price or a quicker sale.

I’m planning to update and repaint, maybe increase rent on one side to 3000-3100 while I live in another unit and replenish to legalize garage space.Monthly payment: $7033. landlord pays for water, everything else is separate.It just feels very tight in the beginning before getting ADU gets legalized. 

I anticipate rent to increase over time.Overall, it's not a bad investment but not stellar, but it was move-in ready, no renovations needed, and essentially pays for itself while it appreciates. 

The lender told me they got no score because I was paying my credit card balance to zero.

In commercial real estate the tenant pays for everything including those pesky condo fees

If you pay all cash, you are paying full price for the property. 

I am struggling trying to decide my next step- should I try to pay down my two current properties that I own as much as I can (I make about 150-200k a year).

Assuming you're not an arborist, you made a judgement call regarding someone else's property and now you are going to have to pay the piper.

I am not usually the smartest person in the room but I like listening to them and paying attention to their advice.

You are paying money thinking it will bring you business, when in reality it's just bringing you a bunch of contacts that aren't serious.Build relationships.