Over time, a good bet would be to save up enough to find a two-family to house hack with lower money down and move there and rent out this one you own outright which would cash flow nicely. 2-1 single-families can be great for mid-term rentals as well which can 1.4-2.5 your cash flow.

Those 4 tend to be the most popular sites for mid term rental listings.

I don't know if starting with a fix and flip would be too formidable. 

Tax benefits can help make a better business deal, but a bad business deal is hardly ever going to break even just because of tax benefits.The other big consideration you should have, in order to actually benefit from real estate fueled losses or credits, it will require a substantial investment of time - either to get over the material participation thresholds for short term rentals, or to get over the real estate professional thresholds for mid term /  traditional rentals. 

I have begun reading David Greene's Long-Term Real Estate Investing to ensure I do this properly.What types of data should I be looking at before choosing a market for mid-term rentals?

As long as you stay in the better areas I think there’s plenty of demand for mid term rentals.  

I think it would be a good candidate for mid term rentals, but I don't want to manage it.

Travelers has a home sharing/furnished rental product that I use for mid terms.

I will continue to look at Springfield and am also exploring Longmeadow and East Longmeadow as I hear that location may be better suited for mid-term rental or rent-by-the-room (CoLiving) arrangements.

We anticipate that demand for mid-scale extended-stay rooms in this tertiary market of Raleigh will continue to rise over the next 5-10 years, as Johnston County is the fastest-growing county in North Carolina.