I did 4 fundings in Janesville last year and my guy got through the first one on time and for profit we expected then he up and passed away from a Diabetic coma.. leaving me with 3 that I had to work out of .. two I sold right away for what I had in them one we made a small profit It happens.I do background checks  dont really care to much about credit but I dont want any criminals and then If they are married I want to meet the wife and take them to the nicest dinner in town.

People date for years and then all hell breaks loose when they get married and move in together.

The only things I feel I need to consider is we will be planning on getting married and I have to pop the big question.

The most important one, as @Tim Ryan points out, is the question of whether the investor is single or married.

Perhaps the county/city would allow you to take over the tax payments but that is up them.

Background:  Late 30s, married with two young kids (4 and 2). 

Under the IRS rules, a person  qualifies as a real estate professional if: (1) more than one-half of the personal services the taxpayer performs in trades or businesses during the tax year are in real property trades or businesses in which the taxpayer materially participates, AND.....(2) hours spent providing personal services in real property trades or businesses in which the taxpayer materially participates total more than 750 during the tax year.Like @Greg Scott and @Russell Brazil mentioned above, I don't believe that you would qualify as a REPS, but if you are going to try it, make sure you document it very well (i.e. with some kind of proof, like time cards, mileage forms, and/or receipts, etc.) so that just in case you do get audited, you at least have something to provide to the IRS agent. 

I used to be convinced that in order to get into the land development business you had to marry a developer's daughter or be born to a developer.

Are you looking to get an investment property at 20% down or a primary residence you can house hack (rent the rooms in the house you are living in), or a primary residence (better for people who are married/have kids/don't want roommates) where you live in it for 12 months then rent it when you buy your next property to repeat the process.

Withdraw your 401k, pay income tax, pay tax penalty, lose opportunity of compounding interest etc - you're taking a huge L out of the gate here Do you have a track record of success?