Have you considered using a 1st Time Home Buyer Down Payment Assistance Loan or Grant to purchase a small multifamily property that you can also live in?

The holes in the boards were there to hold the plaster (because they did not have spackle yet and still had to plaster), just like the wood lathe would. you can repair the cracks just like you would in drywall, i would recommend cleaning out all loose plaster, using a mesh tape and for the first coat some 45 minute easy sand, this product will dry fast and ready for you to put another coat of it or spackle on it, but you may want to solve why you got the cracks in the first place before repairing, usually something needs re supporting. the wire mesh you talk of in the corners can be cut with a sawzall or you can use a drywall hammer and chop it out at the corner ( if your aim is good ) this can be removed and easily patched then with the drywall, just make sure to wear gloves and safety glasses when doing so.

I have started using a spreadsheet but I would like something that makes it easier to keep track of when I have sent the owners a letter or postcard etc; also to attach a picture of the property and some pdf's of county record documents.

It doesn't sound like you're using a multi-family spreadsheet calculator to underwrite your deal. 

This is an instance where possibly using a mortgage broker to shop rates for you would come in handy. 

And are you using a property manager.

If not, have you considered using a 1st Time Home Buyer Down Payment Assistance Loan or Grant to purchase a small multifamily property that you can also live in?

It’s not a matter of using a loan vs. not using a loan.

This is becoming popular.In my view, if you are not using a real lending attorney to keep up and stay educated, you are doing yourself a disservice.

I don't recommend using a real estate agent.