By year end I will tackle a MF, value add with my son that would be sweet if we can swing the coop/tic (handling the finance challenges is the hurdle) so he ends up with a unit at below 50% of retail.  

@Holly Thorsen see above for potential challenges tapping your equity in the rental.You only need 5% down for a regular mortgage, 3% down for an FHA mortgage - so why don't you have the funds?

@John Sherwood The areas you mentioned are certainly high-demand areas, but they come with challenges.

I will be living in the guest house, while renting out the main.Both units are without washer and dryer units, my question is, do I supply them in the main house; or let potential tenants figure that one out?

The power company supplied and installed the new meters (at no charge, at least not yet) and verified all the work around the 4 gang meter pan was done up to their standards.

Over-budgeting is critical to ensure that renovations don’t eat into your profits.Market Fluctuations: If property values in your area do not appreciate as expected, or if you face a market downturn, the amount you can refinance for may be lower than anticipated.Financing Challenges: Securing financing for the initial purchase and rehab, as well as refinancing after the property is rehabbed, may be challenging, particularly if the property is located in an area with fluctuating values or if the rehab work doesn’t immediately improve the property’s appraised value.Tenant Risk: Rent collection and tenant management can be unpredictable.

Challenges?

@Mindy PerryReally doesn't matter what software you pick as long as it has the features you want.Two biggest challenges with ALL software:1) None are perfect, so deal with the tradeoffs2) Most users rarely put in enough time to really understand how to utilize the software.

Really the main challenge is going to be making sure that your wife understands what she needs to do to document her hours and activities.

@Hank Bank BRRRR is probably want you want to do.Buy, Renovate, Rent, Refi, Repeat.Before you go all in and either find out you don't like being a landlord or you make costly mistakes, start with just the next one.You'll have some challenges with tapping the equity in the townhouse:1) What loan amount can you qualify with your credit & income?