I will refer to this to help me stay big-picture focused initially. 

I'm not personally associated but know the folks and highly recommend them.

The real estate market is strong with property value remaining high. 

I'm looking into multifamily (duplex & self landlording) in my local area to get started, but my tri-state area (CT/NY/NJ) has a high entry price point that I'm concerned with over leveraging myself and losing liquidity on my first deal. 

Unfortunately, I haven't gotten any pictures yet.Here's where I'm at financially: I had $10k in savings, but after some unexpected hospital bills for my dad, it's looking more like $8k now.

One last advice I can give you is that MORE is not better, choose low maintenance high demand locations and the rest will fall into place.

You need to do this stuff because it's too easy for tenants or potential buyers to neglect the water bill, and the Detroit Water and Sewer is high.

Combined this leads to high cost of leveraged purchases. 

I'd also highly advise against ever renting to anyone that has the intention of doing STR arbitrage.

Perform the same task in each app to ensure a fair comparison.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.Run a credit/screening report on yourself.Enter a maintenance request, assign a vendor, and attach a fake invoice.Enter charges to the tenant's ledger.Enter recurring charges and automatic late fees.Sign documents electronically.Run owner reports.After testing a few apps, one should clearly stand out.