Speak with lenders about lending on the project We did; one lender summarily dismissed it because we don't have experience with ALFs, but based off the initial description of the project, a lender who did the loan for my 24-unit apartment complex gave us a preliminary yes. 

As of now I’ve only done preliminary checks on the property and these are the few considerations I have to makeGreat questions you’ve asked and looking at the market as well as the location I can rehab and force the rental price up.

I'm in preliminary stages of buying a lot from a private owner to build a new construction home in the City of Chicago.

That's what I'm using to preliminary check rents, as you get closer to actually making the deal it's probably worth talking to a local Property Management company to get an even more accurate estimate.

They should be able to give you a preliminary answer to whether they can do it within 48 hours. 

I'd like to get to the point where I can work as an appraiser in the summer or at least knock out some preliminary appraiser education for some relevant experience.

It most likely qualifies for a capital gain exclusion (again, details matter, so this is a preliminary conclusion), but you still owe taxes on all depreciation taken for this unit.Both units will generate some taxes.

Preliminary chat he shared the following numbers:30% down required5-6% 7 year fixed then adjustableNot sure if I should try sticking with initial plan of a portfolio loan (to diversify risk in multiple properties)OrDo conventional mortgage for 20% down and lower interest rate

I think your plan will still be solid in the long term, LV is much cheaper than LA from a cost of living standpoint, plus I'd wager your commute will be much better. 

I have only done preliminary research at this point but from what I can tell the cost to build is roughly $200-$250 a sq ft and insurance will run me about $3800 a year.