In writing, particularly when the issue may be complicated and/or stressful.

However, and I can’t stress this enough, get a lawyer.

This caused me significant stress.

For my $1100 a year I get1) All of the contracts and forms (purchase, well/septic/listing agreements, Addenda) updated by a panel of lawyers as needed by case law which is about 50 forms I can use as needed2) Transaction desk and all forms uploaded to that for easy filling online out and authentisign so I can have things signed electronically3) Realist, all property information and county records at the touch of a button and good ARV4) RPR Another way to make quick and speedy comps5) MLS which not only lets me get my comps (so 3 comps to use as a comparison) and all sales past and present6) They do have a portal for my clients to visit and do all autoemailing as things come on the market7) Ekey access8) Market reports and stats at the touch of a button.9) Lobbying efforts as Russel mentioned10) Legal help line to callI do give back and am on the tech committee and attend a number of events, but just for the above the money is well spent.

Both you have to should the additional stress of trying to manage that...Bad: She moves out, you have a month or two of vacancy... but key word is vacancy... ready for new tenant/showings.Worst: She just stops paying rent, you have to go through eviction... she has nowhere to go and it just sucks for everyone.

Honestly, just do what will make you the most comfortable and sleep easiest in retirement.Here are some musings on your other options:1031 Exchange 1 property for 1 property is totally manageable but still can be more stressful than your average RE transaction.

I can say, that while they are marketed as "the easy way to get started in real estate with no money or experience", in practice many (maybe even most) wholesale deals are stressful and maybe not ideal for beginners.It's not to say a beginner can't succeed, but there could be a bit of a steep learning curve.

@Nathan McBride We haven't done too much on this project yet (just closed at the end of last month), but I'd definitely say flips are equal parts fun and stress, haha! 

I have the $5 one without a GFCI test button; you might splurge on the $8 one with the GFCI button. 

Another option if you can raise a fairly significant downpayment (25-30%) and are entrepreneurial and can handle stress (!)