I personally won't be doing them here in MD, but some people specialize in acquiring those types of properties and I would strongly suggest you to attend local meet ups and try to speak with someone who had done it successfully and never got burned.

Knowing this, what types of properties do you believe you will be acquiring using the Subject to method?

For this strategy you have to acquire a building within walking distance of the L.   

And generally, they took longer to rent, longer to sell, cost relatively similar (maybe moderately less) to repair and rehab as other less affordable areas, and had more turnover than desired.I also have a good friend/investor who owned over 100 sfr doors in the Detroit area that they were acquiring amazingly cheap, then rehabbing them.

Seller financing can be a great way to acquire property, especially if the seller is open to it and favorable terms can be negotiated.

I'm unsure how well it is now since it was acquired but Ryan (Founder) cared a lot about his product so I'm sure it's still fine.

Hi Natalie, My husband is content to listen to my goals and okay with me using our mutual funds to acquire our first property, he was even okay with me continuing on this path after my first attempt at a duplex house hack fell through leaving us apartment hopping.

Activity DescriptionTenant recruitmentTenant screeningNegotiating and executing leasesOverseeing repairs and maintenanceCommunications with tenants and vendorsTravel timeResearch for potential rental real estate (pub 925)Acquiring rental real estate (pub 925)Paperwork/bookkeeping/bankingResearch and purchase of materialsRent collectionEvictionOn-site cleaningBill paymentOther:Time SpentDate

My biggest concern is will I be able to easily find buyers of the land I acquire...and can I still acquire good land deals through auctions rather than marketing to sellers?  

Generally speaking, it’s most cost effective to acquire the real estate in the correct deed holder entity on day one as it becomes costly to transfer property.