Older homes are harder projects. 4) Make up your lack of experience with other strong compensating factors like good credit, liquidity, and a solid game plan. 

I’m not sure your cash reserves but targeting 2020 to 2022 is the best strategy because there’s likely 0 equity in those and they typically haven’t appreciated enough to have to finance a second line of credit.  

I have some telling me that I can do minor repairs on the property and use a credit card to purchase materials (HVAC Filters, caulk or even paint) and my IRA can pay the credit card directly (keeping it at arm's reach).I also see where this interpretation of services versus repairs could be considered a "Grey" area and I am just looking for something that turns it at least a little darker.

I have rescued a bunch of those investors in my day.I get the sub too attraction I just think those sellers with stellar credit that want to keep their stellar credit take a very big risk giving title away to an asset that they are on the hook credit wise for ... and especially in default judgement states..

Perform the same task in each app to ensure a fair comparison.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.Run a credit/screening report on yourself.Enter a maintenance request, assign a vendor, and attach a fake invoice.Enter charges to the tenant's ledger.Enter recurring charges and automatic late fees.Sign documents electronically.Run owner reports.After testing a few apps, one should clearly stand out.

I would want a concession on the sale price or a seller credit for this so that I can try to end up a little ahead for the hassle and also to keep the deal simple.

When you return an item, if it's on a credit card, you can just enter a credit card transaction for a refund and apply it to a COGS account. 

When you go to refinance, the lenders will have to base the value on the lowest listed price..

With that being said, a portion of the lease can typically be credited towards the purchase price. 

In my experience the basics for a functional RE based CRM are:Custom Fields for Data Objects (Leads, Prospects, Applications, Buildings, Units, etc...)A Screening Engine (background/credit checks, employment verification, etc)Online Rental Application (this should automatically run the application through screening)Ability to mass email/sms leads and tenants to provide informationSurveys/Inspection formsI've been building real estate CRM tools for years.