We did consider/evaluate that option, and have done multiple flips, but at those points have been under contract since New Year's Eve and carrying costs for another 2-3 months without a guaranteed sale is not the risk we want to assume.

At the end of the day I'm ok with taking the slower path of saving up the cash for the down payments and buffer but if there's a quicker way that I'm not aware of I'm open to all options. 

I could budget for saving toward a rental just like I budget for groceries.

The land, however, may appreciate, which can offset this.If you’re in an area where affordable housing is in high demand, mobile home rentals can be an excellent option, especially since you already have the land.

I am not friends with these sellers but these sellers know that I am the best there is at what I do. 

Legal RequirementsIndiana landlord-tenant laws are generally landlord-friendly but require you to be diligent.

Feel free to reach out with any questions about loan options or how I can support your real estate journey!

I got the property off-market for $250k from a trusted family friend.

Your other option is to test it out and see if you can make it work. 

Since you're looking to house hack your first multifamily in New London, CT, or Greater Boston, connecting with local investors and learning about financing options will be key.