I live in New York and ideally my first home should be here so I can manage it myself BUT properties in NY have gone up.

The process was NOT easy.I had to submit:2 years of tax returns for all my businesses, P/L statements for all businesses for past 2 years, P/L statements for all businesses for current YTD, Invoices to prove businesses are still open and operating, E-file tax receipts for 2019 for personal and all businesses, Recent bank statements for personal and all businesses, Etc. 

Is it better to do it one by one (rental, residential, or equal) so that I have a better d/e ratio or can i do it all at once through different lenders?

Lots of details missing such as are you married, kids, debts, savings, renter or homeowner, house-hacking, etc. but ideally just save 6 months living expenses and go full-time agent and forget the 9-5. 

I would try to do it under a self funded IRA ideally but there are prohibited transactions rules going that route.

@Jean-Paul E.

You do get to write off your expenses against your positive gains though so ideally you would like to have your property depreciation write off your yearly profits and get the ancillary benefit of personal use.

I consulted with a BP member a few weeks ago about how to find hidden gems in her town of Nashville and BOOM she sends me an e mail  YOU MEAN LIKE THIS   I said YUP.. thats Money..  

Its a small loan, so I'd imagine fees are high but...My apologies, I just reviewed with the lender and the major fees are:$2,850 origination charges$1,100 underwriting fee$1,949 transfer taxes$2,310 property taxes and homeowners insurance$900 homeowners insurance premiumTotal Loan Costs (A+B+C): $6,220Total Other Costs (E+F+G+H): $6,169My FICO is 714

The trash pickup does come each week, bi-weekly trash could be done but each week is ideal.