I was a Realtor for a short while but needed to get a steady income and health benefits back when my wife and I both started realizing our health issues were very unstable.

The common phrase I've heard over the years is the best time to buy real estate "was 10 years ago".If you buy with cash flow and have financing that doesn't have a short-term balloon, you should be able to ride out any storm and be positive on the other side.

I'll be down there this weekend as well - see my post from yesterday, I was considering putting a meetup together but will be short on time with all the shenanigans going on this weekend. 

So questions to the veteran developers here:1) How do you do your numbers so quickly as to decide if a parcel/lot is worth putting an offer on in such a short amount of time?

This would definitely make it worthwhile to sell, because I was all-in for Duplex C for $165K, can perhaps sell for $185K after closing costs, and that would put me at $20K profit (which will be taxed, short-term ordinary income bracket). 

Long story short, this doesn't look like a deal no matter which way you slice it.

Run the numbers to see which is better short term and long term.Another option is to bring someone in with the down payment.

There are social courtship rituals that you have to go through, casual dates and short relationships you have to live through.

Planning should be like that.At the moment, depending on where you operate, inventory for updated homes tends to be in short supply, so it almost doesn't matter when you list.

Some HOAs may not allow rentals or short term rentals.