I do list at around 90% of market rent to attract interest and select great long term residents. 

Follow-up, Follow-up, Follow-upMost people who use DM as a strategy give up after the first mailing if no one calls.As you map out your strategy, make sure you budget out how many mailings you can afford and select a list that clearly targets your audience.Not all lists are equal, I pull my list from Yardi Matrix.

If I were in your spot I would get in touch with Dominic Delgado or Matt with MJA Real Consulting. 

Aside from providing the basics (ie. listing tool to get the property published to 10+ major sites, scheduling tool to schedule viewings, tenant screening with comprehensive applications -- pulled reports from TransUnion, which include nationwide criminal background checks + credit checks + eviction history, digital lease creation tool, rent collection tool), automated maintenance tracking is key (and having everything in one spot makes a world of difference when it comes time to have a contractor come in and make a repair).

Since you have a very specific tax situation you're trying to plan for I would work with a CPA before you initiate this stock sale to make sure you're in the best tax spot possible. 

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A secret spot to consider would be Point Loma, it abuts the airport, has old school charm, incredible new Liberty Station mega multi-use complex of restaurants and shops, and some awesome big remodeled homes, you could get a ton for $4M.

If the properties on 3 different parcels, and you use conventional financing, I bet they make you use 3 different loan spots. 

Is it too risky to do my very first deal during this pandemic in a virus hot spot?

Any portfolio lenders comfortable lending at 70% with half term IO, 25-30 amortization, and limited P&I/tax/insurance/replacement reserves would be right in their sweet spot.