If you can't close fast enough or has too much red tape, then you lose the deal to others.

Every room occupied for sleeping purposes by one person shall contain at least seventy (70) square feet of habitable room area and every room occupied for sleeping purposes by two (2) people shall contain at least fifty (50) square feet of habitable room area for each person.

Bay Park / Clairemont / Carlsbad / Oceanside are all top-tier markets that fetch top dollar (see the Yellow & Red).Move your search slightly inland, or further down South and inland, in order to get something done for 1/2 the price, with similar rents (not quite as high, but definitely not 50% less like the purchase price would be)

@Cole HarrisKeep in mind that square footage has a lot to do with pricing as much as bedroom count and/or revenue. 

However, like any market, success depends on selecting the right neighborhoods and building a solid team on the ground.In Indianapolis, areas like Broad Ripple, Fountain Square, and Irvington have seen strong appreciation and rental demand, but they can be more competitive.

As Marshall said we will need to know breakdown between residential and commercial, exact business types, and square footage + income breakdown for residential and commercial units.

Are there any potential red flags I should be aware of?

I just paid my attorney 15k today in just fees for 4 entitlement contract red lines and we arnt even under contract yet!  

Reposition the property to a higher and better use. 4 years ago we purchased a 10,000 square foot building used as a music school.

Depending on how upscale your finishes really were, you could have that built in this market for 300 to 325 per square foot fairly easily right now.