Today was supposed to be my jumping off point, but it's been postponed into next week due to weather (seriously...outside business in FL, can't help it) . 

Much more so than so California which is always Spring weather!

I wish I had the gut to be as aggressive as you but I'm forecasting hitting my goals in 7 years in which when I run the numbers more and more the BRRRR strategy appears to be the best and safest bet.

I said we would consider doing this if they could provide a forecast.

In my opinion, you are in the best market for appreciation, as 2018, Las Vegas came in at #1, 10.2% This year, LV is still in the top spot, but forecasts has LV around 7-8%.

If the original incoming service wire is only for 60amps you will need to replace that to the meter & then up to the weather-head & that wiring is heavier & the run can be expensive if you need to include conduit.A new panel will depend on the demand & for the number of circuits, along with double poles for central a/c, electric stove or electric double oven plus stove top, electric dryer & maybe the feed to a garage sub-panel etc.

If it was installed in cold weather that can cause issues also.

They don't call it the windy city because of the weather.

You'll have to weigh weather the trade off of losing $2000/mth is worth holding out and hoping it appreciates enough that you don't lose on the sale.

Now that the cold weather has hit I've come to find out the heating system was done as a hack job that needs to completely get redone - and ASAP.