I realize I could cash in on any of the above and decrease the new mortgage in turn lowering my dti but my intention is to not face any tax losses by selling from any of those accounts before the end of year.

That decreases the amount of money I would be approved by a lender to purchase a property.

The additional amount in yr 1 was to help decrease the initial downpayment-Tenant responsible for all maintenance (but I did purchase them a home warranty to use)

One thing that I have gotten from BRRRR is that if you "buy right", you significantly decrease your chance of getting into trouble.

Since the value of the property should remain static at best and might actually decrease over the time involved and the highest bid amount probably would not increase, any overage going to the OP will decrease. 

In this time of expectations of rate decreasing I dont recommend buying points.

If there is a downturn, estimate if your property can whether the storm with a certain percentage of decreased rents and increased vacancy.I have reduced my buying but I am out there building my network and expanding my target area.

Those investors who want the LLC but won't pay for it (ie move Title back and forth and get commrecial fiancing) APPEAR to be messing with their corporate veil anyway.Its up to you, but you should do it correctly.Oh, other issues with moving TItle back and forth include invalidating your Title Insurance policy and decreasing the validity of the Chain of Title by using quit claim deeds.The protective benefits of the LLC are commonly touted. 

We have $100k cash right now and we're trying to figure out if it's worth it to put the cash we have into refinancing Property 2 based on income generated, decreased value, etc.

Only thing I need now is try and decrease the amount of time it takes me to walk through a property and populate the data.