Of course, I would then have to put off for a while (the dream of) buying and living in a single-family house, which is part of the sacrifice I need to make if I want to start generating cash flow from rentals to invest into more properties.

But if you are doing things like index investing, automated investing (dollar cost averaging), and/or doing your research to pick so called "generational" companies and HOLD these stocks for the long term, it's less gambling and just part of investing.5)  House hack like crazy before you get married or if already married before you have kids.   

It generates a lot of renters.

That doesn't have all the contact details, but they can build their list off the buyer names generated.   

Should I wait until the rehab is 100% finished or start to advertise a property that is undergoing rehab and try to generate interest that way.

@Rodney Kennedy I think you'll be ok on generating leads.

Use the $ you would use to pay down the car to help buy a property that'll generate far more money then the car costs you. 

If you truly want to be successful at lead generation you need to look into becoming more credible than anyone else, as that directly relates to providing value to your traffic.

I think I could build a successful portfolio there, but not one that's going generate the level of income that I want long term, so I'm thinking to start there and diversity into another more expensive market later. 

Windsor is a great "small town" that generates good cashflow with moderate chances of appreciation (relative to the CT Market)Granby even a smaller town feel than Windsor, rentals are in high demand and rent prices are high.