If you can swing the extra DP then yes you should go with the conventional.

I would try to get with an investor in your area for help with the deal if you can't swing it on your own.

I’m more comfortable with the home values in the Midwest, and their general insulation from wild swings in value.

I am a dentist by trade, but looking to expand my portfolio into SFR and multifamily investment properties.

You should swing by, it is next week. 8pm. 

As long as your Comps are accurate it could be a decent deal, but if the pendulum swings to a $290k sale price, there may not be much profit left.

Justifying it by saying “yes you pay for some heat but in trade off you get access to a very efficient AC unit in the summer that you don’t have to install/uninstall/store every year.”

In my area, there's at least a minimum service fee (usually about an hour's time for any trades person) to come out and assess/fix something.  

This way IRA's involvement is completely passive, you can agree on the terms (interest, points, etc.) and all of the income/gains for the IRA will be sheltered from taxes.According to the IRS rules if tax-exempt entity (an IRA in this example) receives income from an active trade or business (which would probably be the case if you JV instead), such income would be subject to Unrelated Business Income Tax.

I'm in Waco, so probably closer to $90 to $100, but we have a lot of visitors (2nd most in the nation right now), so I'm sure I could swing $600 / mo in rentals and break even.2) Nothing extra required, but I would opt into Turo's $1M liability policy.