Milton and Farmington can be excellent choices, too, often with more budget-friendly options and the chance to add value in less saturated areas, might have better cash flow luck here.For lenders and agents, I'd recommend networking with those who have experience specifically in the NH Seacoast markets since these towns can vary in terms of tenant demographics and rental demands.

The issue I have and would like to hopefully get some advice on is the below:In real estate specific tax strategies - it is my understanding that I would be able to generate significant “losses” through the use of bonus depreciation and other strategies. 

Happy to connect if you have specific questions.

You might want to join groups or forums specifically for private lenders—BiggerPockets is obviously a great place, but local REI meetups or masterminds could also help.Also, consider sharing insights or case studies from deals you've done (if you're comfortable) to spark conversations.

Of course a lot of depends on the specific market you are in. 

Probably TMI there lol, but hope that helps a bit.I am also from NW Chicago suburbs - Elgin, to be specific. 

Therefore, I have a hard time committing to a house hack which contributes greatly to my problem of raising capital for a conventional mortgage with a 20%+ down payment instead of alternatives such as an FHA. 

If you have an Iphone, you can create a separate folder for your photos which you can save your business receipts.An alternative option is using an online storage platform such as google drive, dropbox, etcBest of luck

There's also a Q&A section where you or your bookkeeper can write questions for the property manager for specific tenants. 

If you have specific questions about property management, I'll be happy to help!