Knowing this, I had very few reservations about going in on this deal with him.I quickly noticed that my friend, and now investment partner, was not actively engaged in our investment.

Even when you want real estate information unrelated to the property they manage for you, they'll be more obliged to help you.More liability is passed on to them since they are the ones engaging the tenant.They are likely to screen tenants better than you can.They don't dictate rent increases, you do.  

No, we don't engage in affordable housing; quite to the contrary; at this point (after 15 years I should mention) we have been going up further in size and price point.

While I realize that residential GC's will want a faster turn around time, I share this so you know that you are not engaging in inappropriate business practices by demanding that work not be paid for before its finish, and potentially even holding a "retainer" of 10% of the completed work, to incentivize the contractor to actually finish the work. 

I would recommend getting a property under contract, deposit EM, engage lender, hire securities attorney, raise funds, review title/survey, leases, get loan approved, close on property.Reg D raise for sub $5m will probably be $15,000 plus filing fees. 

This project was hard to finance b/c it's an office and lenders were having trouble with engaging resi appraisers to handle this valuation of an existing office bldg.

@Katie Lyon if cashflow is your primary goal in the near future, you are willing to learn an active biz,you have time freedom to engage issues occasionally, you like hospitality, you are motivated enough to learn how to self manage remotely if needed, then I would encourage you to consider the STR biz. 3-5 well selected and performing properties can retire most people from their W2 job.

When a tax-exempt entity engages in a trade or business on a regular or repeated basis, the gains are treated as taxable Unrelated Business Taxable Income (UBTI). 

Some accountants offer free introductory consultations, however there's no way such free engagements can cover the necessary ground.

The seller's agent is very engaged in the area to ensure they maximize the deal for their client.