For years I've been try to find or start my own business, but it's tough to leave a steady paycheck to hope and wonder if any of my crazy ideas would provide the necessary income to have a comfortable life.

IMO, it is better to take real estate investment slow and steady than risk more than you can lose. 

The coaching also helped keep me motivated and accountable with my progress.  

I have a steady well-paying job and good credit but my DTI is quite high (currently owe one years salary in student debt).

And or if I want to make a fee I broker it with my licenses.What I think is really hurting the industry and or the quasi profession of wholesaling is unleashing these newbie type folks who then use weasel clauses and just sling stuff up on the wall hoping something will stick.. god for bid they risk 1,000 dollars of EM.I see RE as being a progression of knowledge and I understand folks have to start somewhere but I for one have zero interest in going through one's learning curve.Just like your core competency of tax sales etc..

I also know Progressive's home owners product can handle rental properties.

Please keep us updated on the progress.

If it's allotted for more value, it will likely help your LTV standard.I would definitely like to see the progress of this project but also help with the financing, if the chance is given. 

Also not to bet on appreciation but I feel Winooski has been on a SLOW but steady upward climb in regards to home value and rents which personally I would take over a market that swings both ways.Best of luckGrant

You probably want to target retiring landlords who are looking to retire and are looking for a steady income stream without the headache of having to deal with the property.