My plan was to buy this and live in it for a bit, but then eventually rented out as my first investment property. 

Wis Dells is a prime location for STRs to be eventually banned or very highly regulated given the large resorts with deep pockets and a lot of influence. 

If they have a property which has zero demand they will simply fail to benefit from it and eventually be forced out of business (unless they have endless time to keep doing what doesn't earn them a penny).

You could look into converting pre-tax money into a Roth IRA, purchase real estate and then all income and profits from sale, are tax-free in Roth IRA.

On top of that, Section 8 tenants are more trouble than the average paying tenant, and they are more likely to create costly turnovers when they eventually leave. 

I am not aware of anyone who solves problems in a lasting way without a cash-flow positive business.Competitors and other solutions will have to monetize, eventually, in one of the following ways:- Make money raising capital themselves, and therefore be another GP (Fund of Funds)- Make money raising capital for sponsors - Make money serving LPs by charging LPsThe free components of PassivePockets will be supported by advertising dollars from sponsors.

But the most common giveaway is that they ask strange questions inquiring about your home and will eventually want you to take it off platform, ie.

Maybe look into properties that have 3 or 4 bedrooms with 1.5 baths and the potential to convert the half bath to a full bathroom. 

What strategies can I implement to maximize rental income from my first property, which I intended to convert into two units ( Unit 1:Main house, Unit 2: Basement sun room) but cannot due to zoning restrictions? 

The were clearly mansions at time of construct, and now converted small multi's all sec8.