I'm sure there's other stuff you'll want to factor in - what businesses are moving to and from each areas. 

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

For me once I've identified the target market/ideal guest, my rule of thumb is if enhances their stay/they'd pay extra for it splurge.

The ideal property would meet the above criteria, AND would have a large yard, or ideally, a detached garage that was a suitable candidate for an ADU construction project (CO now allows ADU construction on most properties), and/or a primary structure that had lots of value-add potential. 

Overcoming Common Financing HurdlesMortgage brokers excel at tackling challenges that often derail new investors:Low Down Payments: Brokers can find lenders offering low or no-down-payment loans, ideal for new investors with limited capital.Complex Income Streams: If you’re self-employed or have variable income, brokers can identify lenders that accept alternative documentation.Competitive Rates: Brokers have the leverage to negotiate better rates and fees, saving you thousands over the life of your loan.Pro Tip: Communicate your investment goals clearly with your broker so they can tailor their search to your needs, whether it’s a short-term fix-and-flip loan or a long-term rental property mortgage.3.

If you are just getting started here in Chicago, house hacking is the ideal situation.

If a property needs too much work upfront, it may not be the best first investment.4.Factor in property management costs—even if you self-manage.

Factor it into your cost and decision. 

I understand there are some other factors I glossed over like gaining the approval of the first seller to switch collateral and the lien in second position, gaining approval of the second seller to put a second position lien below the big loan, and scheduling the sale of the first property to coincide with the purchase of the second property.

That style of learning and introduction to true industry catches my attention as having someone in the space that understands the space to bounce things off of and learn from seems to be the ideal way.I have through a handful of the webinars and follow up calls with different companies and they all basically pitch similar ideas and strategies.