Now it's much harder unless you go for "less desirable" parts. 

I don't own notes, but I do share your desire for totally passive income.

Depending on your desire of how active you want your role would determine which way is better for you.

They also offer the flexibility to package multiple homes together in the same loan if we desire, but the terms remain the same. 

Keep in mind this house is in Southington, CT and is a B+ area (a very desirable area to live) which has a big impact on the rehab and the way it is structured.Draw 1Replace 1st floor gas furnaceInstall new gas furnace and ductwork for floor 2 Replace both hot water heatersPlumbing repairs/modifications: water lines, waste lines, & relocate washer/dryerElectrical repairs/modifications: relocate washer/dryerTotal Amount for Draw 1: $15,000Draw 2Remodel 2nd floor unitFramingPatch and PaintFlooring throughoutKitchen remodel: add cabinets, install granite countertops, backsplash, install appliancescomplete bathroom remodelInstall new light fixturesTotal Amount for Draw 2: $10,000Draw 3Install vinyl sidingPaint exterior trimgarage repairsfront porch/walkway repairslandscapingTotal Amount for Draw 3: $10,000Draw 4Remodel 1st floor unitpatch and paint interiorFlooring throughoutkitchen remodel: new cabinets, new countertops, backsplash, appliancesinstall new light fixturesTotal Amount for Draw 4: $10,000Total Budget = $45,000

Often the transaction costs and time required making selling to move up less desirable than finding other ways to fund new acquisitions if buy and hold is the goal.

For my first real estate investment I've decided to wholesale my first property, and after searching for properties in my desired area, I located a few but they're all on Auction.com, which brings me to my questions.

You already have one great team member in place, and if you have a true desire you are on your way.

I agree with you that a multi step mailing campaign will always out pull a once and done, however, if this is your first campaign and you have a mentor that is doing what you aspire to, I might defer to her.You can do exactly what she says to get her results (if they are desirable to you) and then improve on what she is doing from there.Early on I had a mentor who I listened to exactly and I owe a large portion of my early success to listening to his advice verbatim.

Based upon your courage to have two rentals by 20 and your desire/ability to leverage your artistic and hands on talent to improve projects you will certainly go far here and be a valuable asset to the local community.