With some low interest terms, it could make sense.Best of luck to a fellow Iowan!

The VA lender handbook adds more than 60days may be considered reasonable if both the following conditions are met:1. theveteran certifies that he or she will personally occupy the property as his orher home at a specific date after loan closing, and2. thereis a particular future event that will make it possible for the veteran topersonally occupy the property as his or her home on a specific future date.Can anyone vouch that tenants in place on prior leases and  "a particular future event" being the date in which their lease ends would meet these criteria?

Property was well-maintained by a long term owner (35 years) but it is "dated".  

I've worked with lenders for Cash-out and I couldn't pull enough from the two.I'm working with several APLenders and a few are trying to make it work with my Construction Company and/or personal but it's real close and the closing date is creeping.  

I have a scenario where there is an overlap with (current) outgoing tenant move-out and incoming tenant move-in dates during the middle of Jan 2022. 

I wonder if any fellow members have any experience and are willing to share.

@Dave Spooner Absolutely, the potential of decreased turnover from having a more desirable up to date property can also have a large impact on consistent cash flow!

I would like to hear what other fellow landlords have done in similar situation, should I allow the guest to stay for 30 days or should I tell my tenant, their guest can stay 15 days max.

You may be able to get a non-refundable option payment from the tenant-buyer and can potentially contractually lock-in a premium above the market value on the future sale, which may prevent you from losing money on the resale, if the buyer can actually complete the transaction at a future date.

There is no reason to get married without dating first.