@Hide Harashima It does help, I have been in the hospitality biz in Hudson & Catskill for a decade, NYC before that, converted careers and excited to invest in an area I know and cooked for !

I think you have no choice but to convert to cash yourself.....no one is going to take the risk/hassle of converting afterward.

Converted it into a 3bed 2 bath.

I'm looking to purchase my first property with my fiancé (both 25) with the goal being to establish our primary residence together, as well as giving me the opportunity to add equity/value via rehab before moving on and converting the property into a rental within a year or so to kickstart an investment portfolio.An interesting lead that recently came up is my parent's neighbor's house.

@Matthew Samson, The conversion into a rental and then 1031 can actually be used with the primary residence exemption as long as you watch your dates.Your parents move out for a year and convert the property to investment. 

The layout also has the possibility to convert to a duplex in the future.

Your starting depreciable basis should have been the LOWER of what you paid or the FMV in 2010 when you converted it to a condo. 

Purchase price: $932,500 Cash invested: $450,000 20-unit building converting from LTR to fully furnished MTR/STR.

(An LLC can be converted into in S-corporation.)In order for this to be a sale, you need to get paid its current FMV by your S-corp.

If house hacking has been successfully executed, have you considered exploring a new house hack opportunity and converting your primary residence into a rental?