My question is whether it’s a bad idea to put 20% down and continue renting my own place because of the convenience factors including being able to walk to work (and I work long/late hours).

The (implied - recorded in Wake County) 1997 CCRs predate the North Carolina Planned Community Act but many sections of this Act pertain "to all planned communities created in this State before January 1, 1999." 

Most of us, including myself are not fans of this. 

However the repairs he is asking for include hiring a structural engineer because he believes the foundation is crumbling. 

Did this include the exterior or only interior?

Is this include exterior as well?

Both properties fall into Class B- category and has no HOA and no rental restrictions.Here are the details for each property:Property 1:3 Bed, 2 Bath (1020 sq ft)Purchase Price: $250,000Moderate rehab needed (Kitchen, floor, bathroom sink vanity, light & fan fixtures, interior paint)Rehab Cost: $30,000After Repair Value (ARV): $295,000Down Payment: 20% (Out of Pocket: $50,000 + $30,000 (rehab) = $80,000)Projected Rental Income Post-renovation: $2100/monthProperty 2:2 Bed, 2.5 Bath (1168 sq ft)Purchase Price: $230,000Moderate rehab needed (Kitchen, floor, bathroom sink vanity, light & fan fixtures, interior paint)Rehab Cost: $30,000After Repair Value (ARV): $295,000Down Payment: 20% (Out of Pocket: $46,000 + $30,000 (rehab) = $76,000)Projected Rental Income Post-renovation: $1900/monthThe location is moderate, with amenities like shops, restaurants, a mall, and a baseball stadium within a 5-mile radius.Considering buying both as they are in the same building, the total cost and income overview would be:Total Price for Both Properties: $478,000Down Payment & Closing: $96,000 + $10,000 = $106,000Total Renovations: $60,000Total Price (Including Renovations): $478,000 + $60,000 = $538,000Total Out of Pocket: $166,000Projected Gross Rent Monthly: $4000The rate of interest for the mortgage is 7.5%.I am currently evaluating: A) The break-even point for two townhomes considering a cash investment of close to 32%.

Normally, it'd have to be a loan to yourself which only creates more debt reducing your financing ability. 

It is better to create a separate bank account just for your rental activities.The reason is that it will be easier for you to recognize what is income / expenses more easily.

To create cashflow after rehab the rent is increased to market price and that tenant is unable to afford new rent.