I want to understand my possible options to get started with real estate. 1) Should I buy my first house first?

Check in with @Joseph Chiofalo for help with structuring and evaluating several options.

Any other possitive factors  - stable tenant base  - alarm systems  - regular checks on the property  - no pets  - Lead safe certification  - newer roof, plumbing, electric, etc..Anything to balance off the lossesBe prepared that it may end up in a non-standard (surplus lines) market for a couple of years.If you did not have flood coverage before, see if they will continue the current policy if you get Flood coverage and increase the property coverage deductible. 

The kicker is he now realizes he's out of options and is emailing me that he's going to "win be back" and "convince me to stay" like this is some high school romance.

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provides support for the property tax appeals process.

Your entire price will be based on how many square feet you have as well as color of granite.

And I still didn’t base the purchase on the ratio of property to land, but upon the cash flow the property produces.  

This deal is based off a real tax deed auction property in FL:1912 Sq ft 3/2 SFH in Bay County- ARV: $415,101- Estimated Monthly Rent $2,984- based off 6 comps within a 1 Mi radius.- Adjusted Purchase Price/ Max Bid: $210,840.80- I start with the 1% rule (thus why I start the analysis by looking at rent) and then adjust the price based on the potential pay-out from a cash-out refi and equity position on the property- more on this in a second. - Potential Investor payout (15%): $242,466 - Rehab total: $76,480.00- I just used $40/ sqft for an estimate.

My first investment was a Sandwich Lease Option. 

I'm not sure where they might have been looking but 4 points seems a bit high based on what you just mentioned above.