When you add that: "The downpayment and closing costs would be one large hurdle"; I can't tell if you can only afford to do this once (thus tying up whatever you have saved) or multiple times.  

I understand I can increase liability in each individual landlord policy, but one single umbrella policy is much more cost effective when I have multiple properties.

Assume that you're sitting on:$200,000 in suspended passive losses$150,000 in business losses$100,000 in expiring NOLsThe Magic Transformation:That $500,000 of "painful" ordinary income becomes your strategic advantage:Absorbs all $450,000 of those otherwise-stranded lossesLeaves you with just $50,000 net ordinary incomeMeanwhile, your §1250 gain still gets preferential rates:$581,820 at 25% max (unrecaptured §1250)$700,000 at 20% max (capital gain)The Plot Twist:What looked like a tax nightmare actually solved multiple problems.

Would a bank even allow us to mortgage multiple buildings on a single lot without it being subdivided?

If you stay in one market for multiple investments it may take you a bit to find this particular inspector.

I’ve been a real estate investor since 2015, owning and managing multiple multifamily properties and running a short-term rental business in Cape Cod, the Lakes Region of NH, and the Berkshires.

You want a platform that has built in TCPA protections as well as a multiple communication channels besides voice such as SMS and email.

I lived in Cleveland for multiple months and have some great connections to help you get started investing in Cleveland.

I heard about bigger pockets from a friend of mine that has successfully built and rented multiple properties in our area. 

We have been able to save up some money for our first turnkey multiple unit building.