Would you rather they stop charging you or would you rather they "hold on to" your money until some unknown future date?  

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Hi, we already submitted an offer letter today for a 4-plex asking price $310k (2beds 1 bath) and we are the 1st one to offer them after the previous buyer's financing fell through, the seller agent sounds promising. 2/4 tenant contracts are inconsistent with dates and the seller said that he lives in 1 of the unit which is not consistent with contract dates.

It's a 3 bed 1 bath on each side and the other side is mostly up to date with tenants that were already under lease.

I typically don't have subsequent move-ins scheduled very tightly after move-outs, so when this happens it's more of an emotional hassle than anything else (because the tenant wants to then argue that I'm a monster for charging them rent because life happens . . . c'est la vie).If these one and two day delays significantly derail your process you might consider instituting some kind of "drip reminders" of the checkout process . . . starting 2 weeks before the lease-end date and dripping as often as you see needed to get the tenants out on time.

Read the leases and see what date rent is due and what date rent is considered late.

Does anyone have any suggestions for doing this without the it being structured and feeling forced or like a speed dating event?

As you can see in the image, there is a note stating "15 ft wide unimproved lane as referenced in deed, dated Dec 1818."

The legal owner or mortgage company of the property sold at the sale is entitled to redeem a Certificate of Purchase at any time within four years from the date of the tax sale.

Networking in this way will also help keep you up to date on which areas are improving and you could target.Best of luck,John