And would you recommend it?

You'll want to be able to obtain balances, confirm payments were received, obtain payoff statements, etc.Ask your friend to share the username and password for the servicer's websiteI recommend using a loan servicer to collect your payments and disperse payments each month to the underlying mortgage servicer.

I would recommend just taking out another bridge loan if you need more time to sell, or refinancing into a long term DSCR loan if you do not qualify for conventional loans 

Any recommendations for how to best handle this?

@Neera MelwaniI recommend finding a tax strategist specializing in real estate taxation.

So my recommendation is you want to use a HELOC for situations when you can pay the balance back quickly.

If anyone has any recommendations, experiences, or leads they could share, I would greatly appreciate it!

If anyone has recommendations, please send my way!

The 3-bedroom satisfies neither.I recommend the SFH route, it cash flows just a little nicer.

For your trip next week I would try to meet with a few well recommended and qualified real estate agents to get their estimates on the homes current as is value.