When do Lasso and linear regression have same solution? When do Lasso and OLS give the same solution when applied independently from each other?
But more importantly for me:
If you first run Lasso and say X* are the features that Lasso has not shrunk to zero (so the features that Lasso has kept in the model with a non-zero coefficient in front of it). And then run OLS with these X* (excluding the features that Lasso has shrunk) will you then get the same results (e.g. same coefficients) as the Lasso?
I have this intuition that you will not get the same, but I cannot fully understand why. I assume the L1 term also has effected the estimation of the coefficients of X*? Loosely speaking that observations were used to shrink and thus it is not same as using all observations to estimate the coefficients of X* in an OLS setting?

tl;dr: LASSO is incredibly versatile, but will have different results from OLS. There are many ways to apply LASSO that are used in practice including:

*

*LASSO off the bat

*LASSO for feature selection then OLS

*LASSO for feature selection then picking a different value of $\lambda$ for regression

First, LASSO and OLS will not give the same result unless $\lambda = 0$. They will be minimizing different loss functions (as pointed out by user2974951) and the penalty $\lambda \|\beta\|_1$ will always be pulling it away from the OLS estimate (this can be proved by the fact that you can get the LASSO estimates can result as a Bayes estimate with proper choice of prior and any Bayes estimate with proper prior is biased. OLS, however, is unbiased).
Your intuition is correct. This process of first using LASSO to select features and then running normal OLS on the new model is actually done frequently (when I talked to Trevor Hastie about it he called it "hard LASSOing"), but it is different from just running LASSO and taking the coefficients.
Generally, we can think of LASSO as translating coefficients by a factor $\lambda$ but truncating at zero (this is exactly what happens when $X$ is orthogonal and can be useful to help think about how to think of the effect of LASSO). If we were translating all of the coefficients before, get rid of some of them, and then run a regression without the penalty but on the new variables, then we will get different coefficients from the LASSO estimates because the LASSO estimates included the translation towards zero while the new OLS estimates will not.
Edit: The idea behind using LASSO for just the variable selection step, but not the regression overall is to get consistent estimators (that is, we want to say that as sample size goes to infinity, the estimates converge to the true values, this is generally not true of LASSO).
Another common trick is to do two-stage LASSO or "relaxed LASSO" where you first pick $\lambda$ via cross-validation to do variable selection and then do LASSO again via cross-validation, but after having trimmed the number of features you have. This will lead to lower values of $\lambda$ than with just straight LASSO (so the estimates will likely be closer to the true values), but will also have better generalizability to new data.
