So I think moving the lot lines so the house and 2nd lot can be sold separately or even developed and also doing a moderate level renovation could really increase the value of this property overall. 

This is especially true since I often look for properties that allow for tax grievance potential too further increasing cash flow.

The property value has increased quite a bit since then and i would like to increase it, but i wasn't sure it they would entertain it being that its an investment now and not my primary home.  

Coupled with tailored marketing efforts, these enhancements attracted buyers and significantly increased the property’s profitability.

It was put in place because the feds have increased immigration for the last ~10 years (over 5M people or 8% of our population) to the point that we now have a housing shortage. 

2) Is the extra LTV on cash-out worth the increase in interest rate and if not, how much LTV would I need to go get the next property?

Your insurance is going to be highly variable and I wouldn't use what an agent or the seller tells you as the cost of dwelling policies have increased substantially over the past few years due to rising new construction costs. 

then manage them remotely.you also noted you want an STR, which is going to shrink the inventory that is viable for you and also increase the amount of competition you have.you may want to read these threads:https://www.biggerpockets.com/forums/12/topics/1215726-break...https://www.biggerpockets.com/forums/48/topics/1159104-overl...https://www.biggerpockets.com/forums/963/topics/1195280-expe...https://www.biggerpockets.com/forums/48/topics/1160450-run-i...https://www.biggerpockets.com/forums/48/topics/1137397-balti...i invest in Pittsburgh, and I would tell you: DON'T invest in Pittsburgh unless you're willing to come here in person and build your network. 

The shorter the prepayment term has an impact on increasing the rate.4.

I believe CA market in general is expected to increase by 4-5% but SF is unique.