We have a long-term tenant who has recently started having a guest live with them.

I'd start by talking to your neighbour and asking them to split the cost 50:50 saying that the longevity is reduced because their dog keeps jumping up on it. 

(Before you start reading, I think the overarching theme of this question is that the definition of a Hard Money Lender and Private Money Lender has changed throughout time.

My wife and I are looking for a two family to start with for our 1st home.

And 2) It is like saying...Everyone eats food, so food has huge competition, so it is better to start eating rocks!

I started listening to BiggerPockets just this year!

Should I just start with PM software like RentRedi and deal with everything myself with the help of a local realtor/handyman?

Understood - so say I sell house in Sep-24; then I can adjust my remaining paychecks to catch up to 110% of 2023 tax to avoid tax penalty or I need to start having higher withholdings now?

It includes everything you'd need to start texting (phone lines, unlimited texting, unlimited calling, unlimited users, follow ups etc) without paying for each part on a subscription. 

If anyone has any advice and direction of how best to start, I'm listening.