As far as timeframe, anywhere from 21-45 days depending on how quick a borrower gets their docs to underwriting, how long the appraisal takes, etc.

I would like to pull out equity from the homes to build either a house on each or an ADU (they are zoned multi-family) depending what makes the most sense on returns and what is feasible.

It all depends.

Weather differs depending on where properties are located and even snow accumulation within the same geographic area will vary year to year.

If the client is in CA the community property state laws may help here (not entirely sure) depending on when the property was acquired but it would be a great question for an attorney as Jason mentioned.If they were married and went through a divorce it would be worth looking into how the divorce paperwork stated how that property would be handled.

Plus, other routine tasks like transferring loans and providing payoffs were way more difficult with them than it should have been.

It depends on what the property appraises for in 24 months,  if you will be able to get home owner's insurance, if lenders are lending and so on.

@ Sanjay BakshiHonestly it would depend on the demographics of your rentals.

It depends on the rental income, what you plan on putting down (20-25% is typical, 15% or 25% is required for conventional depending on # of units) For your owner occupied deal, you should be able to use a portion of the rental income to qualify and help offset your DTI a bit. 

Quote from @William Christiansen: Quote from @Charlie Hardage: @Carlos SilvaYa, it definitely works depending on your cash flow and numbers.