You will have to have a professional estimate done.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Whichever strategy you choose, ensure you're adhering to IRS rules about prohibited transactions and working with experienced professionals to structure deals properly.Regarding non-recourse hard money lenders in San Antonio, I don’t have specific recommendations.

Quote from @Polat Caglayan: What do professional investors think about Detroit's course and future? 

Painting, for instance- an amatuer could take their time and paint a house over the course of a couple weeks and do a great job, but a professional crew could do the entire job in a day. 

Readers should seek professional advice.

Otherwise find out if Hawaii has a senior advocate division.

However, we just started STR property management and it would be very helpful/look more professional to have the ability to esign contracts, autogenerate payout statements, direct deposit payouts, ect.  

That would probably require a professional. 

Again, large commitment of time, patience, and ability needed.The amateur of “semi pro” investor should realize that the professional investors (such as myself) spend ALL DAY EVERY DAY doing the above.