Rough calculations on what I need to be looking for:90k deal (purchase and renovations to get max rent)20% down = 18k from me80% bank loan at 8%, 20 yr amortization = 72k-------------------------------------------------- Here's my DSCR calculation:Calculate Net Operating Income (NOI):Monthly rent: $125040% expense ratio (taxes, insurance, repairs, vacancy) = $480NOI: $1250 - $500 = $750Calculate Monthly Mortgage Payment:Loan Amount: $75,000Interest Rate: 8% per year (0.08/12 = 0.006667 monthly)Loan Term: 20 years (20 * 12 = 240 months)Monthly Payment ≈ $627.83Calculate DSCR:DSCR = NOI / Monthly Mortgage PaymentDSCR = $750 / $627.83DSCR ≈ 1.20Therefore, with a $75,000 mortgage at 8% interest over 20 years, the DSCR is approximately 1.20

I feel I have a rough idea, which is..I'm in Rogers Park, my next important step is to wait out 1.5 years until I can fully rent out the condo, but for the meanwhile get a roommate to save more money.

If we use example above (bought the house for $40K and sold for $80K, roughly this is how it would work (excluding closing costs, paid in cash):Purchase price of property: $40,000PML to purchase the property: $50,000 at 6% APRDifference ($10,000) deposited to his account.Property sold for $80,000. $10,000 cash deposit collected from buyer.$70,000 financed as a 30 yr mortgage with 7% interest.Monthly payment to repay $50K PML in 5 years: $966.64Monthly payments collected on 30 yr loan of $70K @7%: $465.71$20,000 in the bank account after transaction closed. 

The current commissioner would allow insurers to use computer modeling of future exposure to set premiums, while requiring them to offer coverage in risky communities roughly in line with their shares of the market.  

They rough house.  

I've also considered just flying back to town and showing it myself as it would be roughly the same cost to do that versus a property management company, if not a less.

For rough examples let's say you are selling your property for $750K. 

Real estate's "gross rent multiplier" is Wall Street's "sales to revenue",  "cap rate" is roughly "P/E ratio".When evaluating markets and investments I tend to start with GRM (or lazily the 1% rule), then attempt to return a cap rate based on assumptions about costs, then I work my way to multiple years of projections (assumptions about inflation, amortization, tax benefits, etc), and if I am partnering with one of my smart friends I have to pull up an IRR (internal rate of return).I also look at regional employment levels, median income to rent ratio in the zip code etc. 

I have roughly $550K in equity and would like to use that equity to invests in more properties.

You can get a decent quality tub without breaking the bank and if you  layout the bathroom where the tub faucet is in the wall you can save some money because floor mounted tub fillers and their rough in are are expensive.